BIBLIOGRAPHY OF THE LITERATURE OF ORGANIC MERCURIALS

BIBLIOGRAPHY OF THE LITERATURE OF ORGANIC MERCURIALS. Frank C. Whitmore. Ind. Eng. Chem. , 1919, 11 (11), pp 1083–1091. DOI: 10.1021/ ...
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N o v . , 1919

T H E J O U R N A L OF I N D U S T R I A L A N D E N G I N E E R I N G C H E M I S T R Y

in view of the cost of wooden vats and the number of such vats required for large-scale production. By choice of suitable acid Concentration the vat space may be cut in half. On the other hand, too much acid renders the solution of the hydrochloride very difficult. 5

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As business conditions approach more and more to the normal, efficiency of processes must he more closely watched. Here is one field where a physicochemical study of the mechanism, velocity, and ultimate equilibrium of all reactions is absolutely

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essential. Thorough physicochemical study can do more toward the determination of maximum yields and quality of the product than +ny other line of work. The time and equipment required to make these physicochemical measurements is frequently overestimated. This has caused some chemists to believe that it is quicker and easier to settle these matters by actual trial in the laboratory or plant. Such a view is incorrect, for the vapor pressures, melting points, and similar physical properties which I have discussed, require no more time or skill than most of the operations of a routine analytical laboratory. We have trained intelligent boys and girls to employ standardized methods for the determination of those physical properties which are most in demand. A complete vapor-pressure curve may be determined in a single day. The data obtained by use of our apparatus and technique have been compared with the results of some of the best experimenters on well-known substances and we agree with them as well as they do with each other. A complete melting-point curve can be measured in two days with an error not exceeding 0.1’. I doubt if the information which can be deduced from these physical daia could be obtained by cut and try experimentation in anywhere near this time. Of course, none of these scientific shortcuts can supplant actual laboratory or plant trial as ultimate proof of a method. They do, however, frequently replace much time-consuming experimentation, NATIONAL ANILINE AND CHEMICAL COMPANY BUFFALO,N E W Y O R K

BIBLIOGRAPHY OF THE. LITERATURE OF ORGANIC MERCURIALS 1

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B y FRANK C. WHITMORE, University of Minnesota, Minneapolis, Minnesota

Received July 21, 1,919

The interest in organic mercury compounds has been steadily increasing during the last few years. This is largely due to the growing feeling among medical men that the much-lauded organic arsenicals are not coming up to expectations in the treatment o f syphilis. This feeling has led to a rather intensive search for organic mercury compounds which shall lack the toxic effect of the mercuric ion but shall retain the marked spirillocidic properties of the element. The publication of this bibliography was prompted by the effort of Dr. A. S. Loevenhart, of the University of Wisconsin, to enlist the efforts of a large number of American organic chemists in the making of new organic mercurials to be tested for possible chemotherapeutic uses. I t is hoped that the bibliography will be helpful to chemists who may becom? interested in this field. The chemistry of organic mercurials has nowhere been satisfactorily summarized or reviewed as has that of the organic: arsenic compounds. A good grasp of the chemistry of the known organic mercurials can only be obtained by mastering almost all of the individual papers. The beginner in the field will be helped by first reading a few articles which contain most of the typical reactions which occur in many of the other papers. Otto1 gives a thorough treatment of the chemistry of merciiry diphenyl. The reactions of this substance are typical of most compounds in which both valences of the mercury are attached to carbon. Pesci2 reviews most of his work published in Gazzetta chimica italiana on the introduction of mercury atoms and groups into aromatic amines. Dimroths studies “mercuration” as a general reaction of all aromatic compounds, as general as nitration or sulfonation. Brieger and * A n n , 154 (1870). 93 Z norg Chcm , AS (1897), 208 a Bet’., 8 1 (1898), 2154, S A (1899), 758; 86 (1902), 2032, 2853.

Schulemannl give a good brief history of organic mercurials and make an exhaustive study of new mercury compounds of naphthalene derivatives, chiefly on the substances which are commercially available as dye intermediates. It will be noted that all four of the articles recommended deal with aromatic compounds. This choice was made because the chemistry of the aromatic mercury compounds is much more definitely known and the substances likely to be of chemotherapeutic value are mainly aromatic. Notable exceptions to this rule are the complex mercury thio compounds which have been recently studied by a number of the French chemists. The first part of the bibliography contains a systematic list of the parent substances from which the organic mereitrials are actually prepared or may theoretically be derived. These parent substances are arranged in the order used in the third edition of Beilstein. By comparing the table of contents in the front of a volume of Beilstein with the corresponding part of the bibliography it is possible to tell a t a glance what classes of compounds are not represented by organic mercurials. It will be noted that the gaps are many and extensive. Compounds to fill these gaps should be made and thoroughly tested for their pharmacological properties. Of course their purely chemical properties should not be neglected. Too much of the modern work on organic mercurials has aimed a t immediate usefulness. The result of this tendency is that we do not know nearly as much of the chemistry of organic mercury as we should, considering the great number of compounds which have been prepared. The second part of the bibliography consists of a series of references illustrating the important reactions of mercury compounds having either one or both valences attached to carbon. J . pro& Chcm., [2], 89 (1914), 97.

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The third and last part contains a n alphabetical list of misoellaneous topics related to organic mercurials. I n some cases there are groups of references which have not been carefully reviewed and arranged but which may be of use t o those interested especially in the medical and pharmacological aspects of the subject. P A R T I-SYSTEMATIC

CLASSIFICATION O F THE LITERATUBE

OF ORQANIC-MEBCUEIALS

The references to the articles on organic mercury compounds zre listed under the parent substances which are arranged in the order used in the third edition of Beilstein. The four “sections” correspond t o the four volumes and the designating numerals SECTION I-MERCURY Mercury Derivatives of Saturated Hydrocarbons METHANE AND ETHANE: I A, p. 100. Frankland, J. Chem. SOC.,3*,(1851), 322; A n n . , 77 (185l), 225. Frankland, Ann., 85 (1853), 361. Strecker, Ann., 92 (1854), 77, 79; Dunhaupt, Ibid., 379. Buckton, Ann., 108 (1858), 103. Buckton, Ann., 109 (1859), 219. Frankland, A n n . , 111 (18591, 57. Buckton, A n n , 112 (1859), 221. Frankland and Duppa, A n n , 130 (1864). 105, 109. Schorlemmer, Ann., 132 (1864), 234. Chapman, J. Chem. Soc., 19 (1866), 150. Sinda, Monatsh., 1 (1880), 716. Seidel, J . prakt. Chem., 121 29 (18841, 135 Berthelot, Comfit. rend., 129 (1899), 379,918. Mathews, J. Phys Chem.. 9 (1905), 641 Franklin, Z . fihys. Chem., 69 (1909), 299. Hale and Nunez, J. A m . Chem SOC., 33 (1911), 1561. Hilpert and Ditmar, Ber., 46 (1913), 3740. Lev and Fischer, 2. anorg. Chem., 82 (1913),-329, 337. Crymble, J. Chem. Soc., 105 (1914), 667. Jones and Werner, J . A m . Chem. SOL, 40 (1918), 1257, 1271. PROPANE : Cahours, Comfit. rend., 76 (1873), 134, 748, 1383; Jahresber, 1878, 518; Ber., 6 (1873), 567. BUTANE: Cahours, Comfit. rend., 77 (18731, 1405; Jahresber., 1873, 520; J . prakt. Chem., [2] 8 (1873), 395. PENTANE: Frankland and Duppa, A n n . , 130 (18641,110 Marquardt, Ber., 21 (1888)’ 2038. Jones and Werner, SJ. Am. Chem. sac., 40 (1918). 1269. OCTANE: Eichler, Ber , 12 (1879), 1880. Mercury Derivatives of Unsaturated Hydrocarbons

ETRYLENE : I B, p. 111. Hofmann and Sand, Ber., 33 (1900). 1340, 2692; Biilmann, Ibid., 1641. Sand, Ber., 34 (1901), 1385, 2906. Sand, Ann., 329 (1903), 138. Sand and Breest, Z. physik. Chem., 59 (1907), 424. Schoeller and Schrauth, B e . , 46 (1913), 2864. PROPYLENE L Hofmann and Sand, Ber., 33 (1900), 1354. Sand and Singer, Bet’., 35 (1902), 3180. Sand and Genssler, Ber., 36 (1903), 3700. BUTYLENE : Deniges, Bull. SOC.Chim., [3] 19 (1898),494. Hofmann and Sand, Ber., 33 (1900). 1356.

AMYLENE: Bull. sac. chim., 131 19 (1898), 494.

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and letters in the margin correspond t o those used in the tables of contents in the front of the volumes. The Roman numeraIs and letter show the p a r t i d a r type of compound dealt with and the page makes it possible t o use the fifth supplementary volume of Beilstein as an index t o the bibliography. T o cite a casesuppose we want t o find whether or not a mercury derivative of anisaldehyde is known. The fifth supplementary volume directs us t o Volume 3, page 81. Page 81 does not appear in Section 4. The nearest reference t o it is “VI C, p. 118.” A glance at the table of contents in volume 3 shows us t h a t not only anisaldehyde but all the other aromatic aldehydes are without mercury derivatives in the bibliography.

DERIVATIVES O F THE ALIPHATIC SERIES

ACETYLENE: I C, p. 127. Kutscheroff, Ber., 14 (1881), 1540. Plimpton, Proc. Chem. Soc., 8 (1892), 110. Keiser, A m . Chem. J., 15 (1893), 537. Plimpton and Travers, J. Chem. Soc., 65 (1894), 266. Pharm. ZentraZhalZe, 37 (1897), 606. Hofmann, Bey., 31 (1898), 2213, 2783; K6thner, Ibid., 2475. Erdmann and Kbthner, Z . anorg Chem., 18 (1898). 53. Biginelli, Ann. d i Farmacoterap. e Chim., 1898, 16; Chem. Zentr., [I] 1898, 925. Hofmann, Ber., 32 (1899), 874. Le Comte, J . fiharm. chim., 161 16 (1902), 297; Chem. Zentr., [ I I ] 1902, 1499. Burkard and Travers, J . Chem. Soc., 81 (1902), 1270. Biltz and Mumm, Ber., 37 (1904), 4417; Hofmann, Ibid., 4459. Biltz, Ber., 38 (1905), 133; Hofmann, Ibid., 663. Brame, J. Chem. Soc., 87 (1905), 427. Nieuwland and Maguire, J. A m . Chem. SOC., 28 (1906), 1025. Biltz and Reinkober, Ann., 404 (1914), 219. Fr. Pat. 479,656, Chem. Abs., 11 (1914), 870; Swiss Pat. 74,446, Ibid., 2027. Manchot, Ann., 417 (1918), 93. Patents, Chem. Abs., 12 (1918). 42, 280,484, 566, 588.

AJ.I,YLENB: Kutscheroff, Ber., 17 (1884), 13.

ISOPROPYL ACETYLENE: Perkin, Chem. Abs., 7 (1913), 2095; Brit. Pat. 277 CYCLOPENTADIENE : Thiele, B n . , 34 (1901), 71.

DICYCLOPENTADIBNE: Hofmann, Ber., 89 (1906), 3188. Mercury Derivatives of Organic II A, etc., p. 141.

Halides

SATURATED HALIDES See work of Frankland a n d of C a h o u n under “Mercury Derivatives of Saturated Hydrocarbons.”

DIHALIDES: Methylene. Sakurai. J. Chem. Soc., 37 (1880), 658. Sakurai, J. Chem. SOC.,39 (1881), 485. Sakurai, J. Chem. Soc.. 41 (1882), 360. Tetramethylene. Braun, Be*., 46 (1913), 1792. Pentamethylene. Hilpert a n d Grfittner, Ber., 47 (1914), 177.

POLYHALIDES : Iodoform. Sakurai, J. Chcm. SOC.,39 (1881), 488. UNSATURATED HALIDES: Halogen Ethylenes. Hofmann a n d Kirmreuther, Ber., 41 (1908), 314. Allyl Halides. Zinin, Ann., 96 (1855), 363. Linnemann, A n n . Spl., 3 (1865), 262.

Linnemann, Ann., 140 (1866), 180. Oppenheim, Ber., 4 (1871), 670. Halogen Acetylenes. Hofmann and Kirmreuther, Ber., 41 (1908), 314. Hofmann, Bw., 42 (1909), 4234. Propargyl Halides. Henry, Ber., 17 (1884), 1132. Reactions of Mercury Compounds with Aliphatic Nitro Compounds I11 B, p. 202. V. Meyer, Bey., 5 (1872), 516. V. Meyer, Ann., 171 (1874), 31. Nef, Ann., 280 (1894), 271. L. W. Jones, Am. Chem. J., 20 (1898), 1, 33. Scholl and Nyberg, Ber., 39 (1906), 1958. Reactions of Mercury Compounds with Alcohols IV A, p. 213. SATURATED ALCOHOLS: Sobrero and Selmi, Ann., 80 (1851), 108; Gerhardt, Ibid , 111. Cowper, J. Chem. Soc., 39 (1881), 242. Hofmann, Ber., 31 (1898), 1904. Hofmann, B e y . , 32 (1899). 870. Nef, Ann., 309 (1899). 171. Deniges, A n n . chim. phys., [7] 18 (1899), 382. Hofmann, Bey., 33 (1900), 1328, 1344. Grignard and Abelman, Bull. sac. chim., [4] 19 (1916), 18; Chem. Abs., 10 (1916), 1525. UNSATURATED ALCOHOLS: Vinyl Alcohol. Semmler, Ann., 241 (1887), 117. Poleck and Thtimmel, Ber., 22 (1889). 2863. Net. Ann., 298 (1897). 316. Allyl Alcohol. Hofmann and Sand, Bn., 33 (1900). 1358, 2692; Biilmann, Ibid., 1641. Sand, Bw., 34 (1901), 1385. Biilmann, Ber., 35 (1902), 2586. Biilmann, Ret. tmu. chim., 36 (1916), 289; Chem. Abs., 11 (1917). 3035. Higher Saturated Alcohols. Sand and Singer, Ann., 329 (1903), 167, 174. Glycerin Compounds IV C, p. 272. Stoehr, J. grakt. Chcm., 121 55 (1897), 83. t a u n o y and Levaditi, Comfit. rend., 153 (1911), 1520. B(lrner, Chem. Abs., 11 (1917), 2600; Ger. Pat. 293.692. Mercury Derivatives of Ethers V A, p. 293. Hofmann and Sand, BW., 33 (1900), 1341, 1350, 2693. Sand, Ber., 34 (1901), 1385. Schrauth and Schoeller. Ber, 43 (1910). 695. Schrauth and Schoeller, E n . , 44 (1911). 1048, 1432. Schoeller and Schrauth, B n . , 46 (1913). 2864. COMPOUNDS FORMED FROM ETHERSAND MERCURIC

SALTS:

Glyceryl ether. [2] 55 (1897), 83.

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Propargyl ethyl ether. Peratoner, Gam. chim. ita!., [11] 24 (1894), 36; Chem. Zentr., [11] 1894, 549. Mercury Lecithin VI[ A 8, p. 342. Schoeller and Schrauth, Chem. Zentr., [I] 1911, 103: Ger. Pat. 228,877. Mercury Compounds from Mercaptans and SulAdes VI1 A, p. 348. Zeiser, Ann., 11 (1834), 114. Otto, Z . Chem., 6 (1870), 22. Clacssen, J . prakt. Chem , [2] 15 (1877). 205. Otto, Ber., 15 (1882), 125. Smiles, J . Chem Soc., 77 (1900), 160. Hilditch and Smiles, J. Chem, SOC., 91 (1907), 1397. IH. 0.Jones, J . Chem. Soc., 95 (1909), 1910. Ray, J. Chem. Soc., 109 (1916), 603. RBy, J. Chem. SOC,111 (1917), 101; Chem. Abs., 11 (1917). 1422, 1423. Mercury Derivatives of Fatty Acids IX A, p. 392. FORMIC ACID: Schoeller and Schrauth, Ber., 46 (1913), 2864. ACETICACID: Hofmann, Ber., 32 (1899), 870. Hofmann, Ber., 33 (1900). 1331, 1345. Dimroth, B e y . , 35 (1902), 2870. Sand and Singer, B e y . , 36 (1903). 3707. Fischer, Ber., 40 (1907), 389. Schrauth and Schoeller, Ber., 41 (1908), 2090. Schoeller and Schrauth, Chem. Zentr., [I] 1910, 1078; Ger. Pats. 218,966 and 219,967; Ibid., 1767; Ger. Pat. 221,483. PROPIONIC ACID: Fischer, Bey., 40 (1907), 386. Schoeller and Schrauth, Ber., 42 (1909), 782. Schoeller and Schrauth, Biochcm. Ztg., 33 (1911), 381; Chem. Zentr., [II] 1911, 707. Schilling, et al., 2. Chemotheragie, 1(1912),21; Chem. Zentr., [I11 1912, 1051. BUTYRICACID: Schoeller and Schrauth, Chem. Zentr., [q 1910, 1078.

FATS: S c h d l e r and Schrauth, Chem. Zentr., 1911, 102; Ger. Pat. 228,877. ESTER: NITROA~ETIC Prager, Monatsh., 33 (1912), 1285. Mercury Derivatives of Unsaturated Acids IX B, p. 500.

[q

ACRYLICACID: Biilqann, J . grakt. Chem., 12161 (1900), 223. CROTONIC ACID: Biilmann, B n . , 43 (1910), 579. Biilmann, Rec. trav. chim., 36 (1907), 289; Chcm. Abs., 11 (1917), 3036. ALLYLACETICACID:

Ibid.

OLEIC ACID: Crowley, Chem. Druggist, 78 (1911), 20;

Chmn. Abs., 5 (1911), 2528 Simonelli, Rass. clin terapia, sci. afini, 1 4 (1915), 329; Chem. Abs., 10 (1916), 951. Mercury Derivatives of Oxyacids X A, p. 552. LACMCACID: Fransois, J . phorm. chim., 15 (1917), 33; Ckem. Abs., 11 (1917), 1258. Mercury Derivatives of Ketonic Acids X B, p. 591. ACETOACETIC ESTER: Lippmann, 2. Chem., 5 (1869), 29. Hellon and Oppenheim, Ber., 10 (1877). 701. Biilmann, Ber., 35 (1902), 2571. Michael, Bey., 38 (1905), 2090.

Soc.,

Marsh and Fleming-Struthers, Proc. Chcm. 21 (1905), 248; Chsm. Zentr., [I] 1906,

229. PROPIONYL PROPIONIC ESTER: Hellon and Oppenheim, Ber., 10 (1877), 700. CAMPHOCARBOXYLIC ACID: X D, p. 627. Chem. Zentr., [11] 1914, 367; Ger. Pat. 275.932. Mercury Derivatives of Dibasic Acids XI B, p. 648. MALONIC ACIDAND ESTER: Biilmann, Ber., 35 (1902), 2583. Marsh, Proc. Chem. SOC., 21 (1905), 248; Chem. Zentr., [I] 1906, 229. Schrauth and Schoeller, B e y . , 41 (1908), 2087. Schrauth and Schoeller, Ber., 42 (1909), 782: Biilmann, Ibid., 1067. Schoeller and Schrauth, Chem. Zentr., [I] 1909; Ger. P a t . 208,634. Schrauth and Schoeller Biochem. Z., 33 (1911), 381; Chem. Zentr., [If] 1911, 707. MALEICACID: XI C, p. 701. Biilmann, Ber., 43 (1910), 579; Rec. trau. chim., 36 (1917), 289; Chem. Abs., 11 (1917), 3035. ALLYLMALONIC ESTER: Biilmann, Rec. trav. chim., 36 (1917), 306; Chem. Abs., 11 (1917). 3036. MERCURYCHOLATE: XI1 E, p. 781. Chem. Zentr., [I11 1906, 385; Ger. Pat. 17 1,485. Chem. Abs., 5 (1911), 1165; Ger. Pat. 225,711; Ibid., 2701; Ger. Pat. 231,396. Mercury Derivatives of Aliphatic Aldehydes XXVII A, p. 914. Nef, Ann., 298 (1897), 316. Hofmann, Bey., 31 (1898), 2213; 33 (1900). 1338; 38 (1905), 2001. Auld and Hantzsch, Ber., 38 (1905), 2684. Lasserre, J . pharin. chim., [6] 22 (1905), 246; Chem. Zentr., [II] 1905, 1125. Biltz and Reinkober, A n n . , 404 (1914), 219, 236. Manchot, Ann., 417 (1918), 94. HEXAMETHYLENE TETRAMINE: Schmiz, Ber. pharm. Ges., 20 (1911), 201; Chem. Abs., 5 (1911), 765. Scagliarini, Atti accad. Lincei, I51 21 (1912); [11], 640; Chem. Zentr., [I] 1913, 705. Scagliarini, Gazz. chim. ital., [2] 43 (1913), 461; Chem. Zentr., [I] 1914, 246. Vanino and Schinner, Arch. Pharm., 252 (1914), 449; Chem. Zentr., [I11 1914, 1195. Schamberg, et al., A m . J . Syphilis, 1 (1917), 1; Chem. Abs., 11 (1917), 1690. Mercury Derivatives of Aliphatic Ketones XXIX A, p. 978. : ACETONE Reynolds, Chem. News, 23 (1871), 217; Z . Chem., 7 (1871), 254; Proc. Roy. Soc., 19 (1871), 431. Denigss, Compt. rend., 126 (1898), 1868; 127 (1898), 963. Hofmann, Ber.,31 (1898). 2215. Oppenheimer, Ber., 32 (l899), 986. Biilmann, Ber., 35 (1902), 2572. Tafel and Schmitz, Z . Eleclrochem., 8 (1902). 287. Auld and Hantzsch, Ber., 38 (1905), 2677. Marsh and Fleming-Struthers, Proc. Chem. SOC., 21 (1905), 248; Chem. Zentr., [I] 1906, 229. Marsh and Fleming-Struthers, J . Chem. SOC.,87 (1905), 1878. Lasserre, J . #harm. chim., 161 22 (1905), 246; Chem. Zentr., [II] 1905, 1125. Tafel, Ber., 39 (1906), 3626.

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METHYLETHYLKETONE: Sand and Genssler, Ber., 36 (1903), 3704. Tafel, Ber., 39 (1906), 3626. KETOXIMES: XXXI A, p. 1029. Sand, Ann., 329 (1903), 181. Francesconi and Cusmano, G a m . chim. itd., I21 39 (1909), 117; Chem. Zentr., [I11 1909, 1341.

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Mercury Derivatives of Aliphatic Amines ALKYLAMINES: XXXIII A, p. 1110. Kohler, Ber., 12 (1879), 2208. Striimholm, Z . anorg. Chem., 57 (1908), 93. Widman, Arkiv. Kemi, Min. Geol., 5 (1913), 36; Chem. Zentr., [I11 1913, 1851; Z . anorg. Chem., 68 (1910), 1. Raffo and Scarella, Gazz. chim. ital., 111 45 (1915), 123; Chem. Zentr., [I] 1915, 1198. ETHYLENEDIAMINE: XgXIV A, p. 1150. Pesci, Gam. chim. i f a l . , 111 39 (1909), 143. Traube and Loewe, B e y . , 47 (1917), 1915. Mercury Derivatives of Amino Acids XXXVIII B, p. 1183. GLYCINE: Dessaignes, A n n . , 82 (1852), 235. Kieseritzky, Z . physik. Chem., 28 (1899), 392. Bernardi, Gam. chim. ital., [2] 44 (1914), 257; Chem. Zentr., [I] 1915, 658. DI- AND TRI-GLYCOLAMIDS ACIDS: Kieseritzky, Z . physik. Chem., 28 (1899), 390. GLUTAMINIC ACID: XXXVIII F, p, 1213. Abderhalden, Z . physiol. Chem., 7 8 (1912), 334. PYRROLIDONB CARBONIC ACID: 2. phrsiol. Chem., 78 (1912), 335. Mercury Derivatives of Cyanoacetic Acid XXXIX A, p. 1217. Petterson, J . prakt. Chem., [2] 86 (1912), 462. Mercury Derivatives of Acid Amides ACIDS: AMIDESOF THE FATTY XLIV B, p. 1235.

FORMAMIDE : Fischer and Griitzner, Arch. Pharm., 232 (1894), 329; Chem. Zentr., [I11 1894, 738. : ACETAMIDE Strecker, Ann., 103 (1857), 324; A n n . chim. phys., (31 52 (1858), 506. Markownikoff, Z . Chcm. Pharm., 6 (1863), 535; Jahresber., 1863, 325; Chem. Zentr., 1864, 415. Oppenheim and Pfaff, Ber., 7 (1874). 624. Tafel and Enoch, Ber., 23 (1890), 1553. Seliwanoff, Ber., 26 (1893). 423, 987. Forster, J . Chem. Soc., 73 (1898), 783. Fiirth, Monatsh., 23 (1902), 1154. Schoeller and Schrauth, Ber., 42 (1909), 784. MONOCHLOROACETAMIDE : Menschutkin and Jermolajew, Z . Chcm., 7 (1871). 5; Jahresber., 1871, 728. Francesconi and Plato, Gaze. chim. itd., [l] 33 (1903), 228; Chem. Zentr., [II] 1903, 24. CYANOACETA~IDB: Ley and Schaeffer, Z . physik. Chem., 42 (1902), 702. PROPIONAMIDE : Sestini, Z . Chem., 7 (18711, 34. Kieseritzky, 2. physik. Chem., 28 (1899), 392. BUTYRAMIDE: Dessaignes, Ann., 82 (1852), 234. AMIDESOF CARBONICACID URETHANES: XLIV E, p. 1263. Pieroni, Gas?;.chim. ital., 121 41 (1911), 754; Chem. Abs., 6 (1912), 995,

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CYANICACID (CARBIMIDE) : A m . J . Syphilis, 1 (1917), 1; Chem. Abs., 11 (1917), 1690. CYANURIC ACID: 2. physik. Chem., 28 (1899), 403. Hantzsch, Ber., 35 (1902), 2717 MUSTARD OILS: A. W. Hofmann, Be?., 1 (1868), 171. Anschutz, Ann., 371 (1909), 201; Chem. Ztg., 34 (1910), 89. UREA (CARBAMIDE) : Werther, J . prakt. Chem., [ l ] 35 (1845), 63. Dessaignes, Ann., 82 (1852), 232. Liebig. Ann., 85 (1853), 289. Ruspaggiari and Pesci, Gazz. chim. ital., [ l ] 27 (1897), I ; Z . anorg. Chem., 15, 231. Pesci, Gaez. chim. ital., [ 2 ] 28 (1898), 474; Chem. Zenlv., [I] 1899, 362. Kieseritzky, Z . physik. Chem., 28 (1899), 393. URIC ACID: Kieseritzky, 2. physik. Chem., 28 (1899), 399. ALLANTOIN : XLIV H. p. 1357. Dessaignes, J . pharm., [31 32 (1857), 39; Jahresber., 1857, 364. OXAMIDE : XLIV I, p. 1364. Dessaignes, Ann., 82 (1852), 233. Kieseritzky, 2. physik. Chem., 28 (1899), 394. PARABANIC ACID: Ibid., 398. : MALONAMIDE Freund, B e r , 17 (1884), 133; 2 . physik. Chem., 28 (1899), 394. SECTION 2-MERCURY

DIETHYL BARBITURICACID (“VERONAL”) : Schrauth and Schoeller, Ber., 43 (1910), 697. Bayer and Co., Chem. Abs., 5 (1911), 3880; U. S. Pat. 1,001,829. Engelmann, Chem. Abs., 6 (1912), 2674; U. S Pat. 1,034,092. Lami, Boll. chim. farm., 53 (1914), 193; Chem. Abs., 10 (1916), 2613. ASPARAGIN : Dessaignes, Ann., 82 (1852), 237. SUCCINAMIDE : Menschutkin, Ann., 162 (1872), 173, Z. physik. Chem., 28 (1899), 394.

SUCCINIMIDE : Dessaignes, Ann., 82 (1852), 234. Menschutkin, Ann., 162 (1872), 171. Landsberg, A n n . , 215 (1882), 209; A m . J . Syphilis, 1 (1917), I ; Chem. Abs., 11 (1917), 1690.

FUMARAMIDE : XLIV K, p. 1389. Dessaignes, Ann., 82 (1852), 233. ALLOXAN AND ALLOXANTIN: XLIV P, p. 1398. Dessaignes, J . pharm., [3] 32 (1857), 39; Jahresber., 1857, 364. I M I D E OF CAMPHORIC ACID: Ley and Schaeffer, Z. physik. Chem., 42 (1902), 703. Mercury Derivatives of Cyanides: XLV A, p. 1409. MERCURICCYANIDE: See Gmelin-Kraut-Friedheim-Peters, 11, 831-846. See Beilstein, 3rd Ed., I, 1414-1416.

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No.

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MERCURICOXYCYANIDE: See Gmelin-Kraut-Freidheim-Peters, V, Part: 11, 849-854, 1728. METHYLA N D ETHYL CYANIDES: Hartley, J. Chem. Soc., 109 (1916) 1302; Chem. Abs., 11 (1917), 575. FULMINIC ACID: See Beilstein, 3rd Ed., I, 1457. Meyer and Rilliet, Ber., 5 (1872), 1030. Meyer, A n n , ,171 (1874), 35. Nef, Ann., 280 (1894), 275. I,. W. Jones, A m . Chem J . , 20 (1893), 33. Wieland, Ber., 40 (1907), 418; Chem. Abs., 1 (1907), 1270. Hagen, 2. ges. Schiess-Sprengsfof, 6 (191 I ) , 4, 31, 44; Chcm. Abs., 5 (1911), 1514. MacDonald, Arms and Erplosiues, 19 (191 l ) , 24; Chem. Abs., 5 (1911), 1516 (History)., Kibler, 8th Infernat. Congr. Appl. Chem., 25, 239; Chem. Abs., 7 (1913), 2117. Wolf, Z . ges. Schiess-Spvengstoff, 7 (1912), 272; Chem. Abs., 7 (1913), 2684. Stettbacher, Z. ges. Schiess-Sprengsloff, la (1915), 193; Chem. A b s , 10 (1916), 118. Chem. Abs., 12 (1918), 2687. Mercury Derivatives of Diazo Acetic Ester XLIX, p. 1493. Curtius, J . praht. Chem., 121 38 (18881, 41 I.. Mercury Derivatives of Cacodyl LI, p. 1510. Schamberg, A m . J . Syphilis, 1 (1917), 1;. Chem. Abs., 11 (1917), 1690. Reactions of Mercury Compounds with Zinc. Alkyls LIV. p. 1522. Frankland, A n n , 111 (1859), 59. Oppenheim, Ber., 4 (1871), 670.

DERIVATIVE 5 OF AROMATIC HYDROCARBONS, PHENOLS, ALCOHOLS AND ACIDS

Mercury Derivatives of Aromatic Hydrocarbons

I A, p. 14. HEXAHYDROBENZENE. CYCLOHEXANE: Kurssanow, J . Russ. Phys. Chem., 31 (1899), 534; Chem. Zentr., [II] 1899, 477. Grtittner, B e r . , 47 (1914), 1651. BENZENE: Dreher and Otto, 2. Chem., 4 (1868), 685; Bm., 2 (1869), 543; Z . Chem., 6 (1870),9; A n n . , 154 (1870), 93; J . prakt. Chem., [2] 1 (1870), 179. Wurtz, 2. Chem., 5 (1896), 385; Compt. rend., 68 (1869), 1300; Ann., S p l . 7 (1870), 128. Ladenburg, Ann., 173 (1874), 151. Michaelis, A n n . , 181 (1876), 280. Aronheim, A n n . , 194 (1878), 148. Michaelis, Ann., 201 (1880), 184. Michaelis, Ber , 13 (1880), 58. Michaelis, Be7,., 15 (1882). 180. Heurnann, Ber., 16 (1883), 1626. Otto, Ber., 18 (1885), 247. Michaelis, A n n . , 242 (1887), 170. Fleck, Ann.,276 (1893), 138. Michaelis., B e 7. . . 27. (1894). -~~~ . . 244:. Krafft and Lyons, Ibid., 1768. Willgerodt, Ber., 30 (1897). 56; Bamberger, Ibid,, 509; Gillmeister, Ibid., 2843. Willgerodt, Be7.; 31 ‘(1898). 915; Hasenbaumer, Ibid., 2910. Dimroth, Ber., 32 (1899), 760. Pesci, Alti accad. Lincei, [I] 8 (1898), 130; Chem. Zenlr., [ l ] 1899, 734. Pesci, G a m chim. ital., [ l ] 29 (1899), 394; Chem. Zentr., [I11 1899, 481. Berthelot, Compt. rend., 129 (1899), 379, 918. Michaelis, Ann., 315 (1901), 29. Chem. Zentr., [I] 1901, 449-454, “Habilitiitionsschrift Ttibingen 1900.” Dimroth, Chem. Z l g . , 26 (1902), 559. Acree, A m . Chem. J., 29 (1903), 588. Peters, Ber., 41 (1908), 3174. Pesci, Gazs. chim. itaZ., (11 39 (1909), 143; Chem. Zentr., [I] 1909, 1092

TOLUENE :

Xylene. Jacobsen, Ber., 14 (1881), 21 12. Jacobsen, Ber., 17 (1884), 2374. Weller, Ber., 20 (1887), 1719. Michaelis, Ann., 293 (1896), 313. Michaelis, Ann., 315 (1901), 20. PROPYLBBNZENE: Meyer, J. prakt. Chem., [Z] 34 (1886), 103. PSBUDO CUMEXE: Michaelis and Sonnenlcolh, B e y . , 28 11895). 591. Michaelis, A n n . , 315 (1901), 32.

Tolyl Compounds. Dreher and Otto, Z . Chem., 4 (1868), 685; 6 (1870), 19. Wurtz, Compt. rend., 68 (1869), 1300; 2. Chem., 5 (1869), 385. Otto, J . prakt. Chem., [2] 1 (1870), 185. Dreher and Otto, Ann., 154 (1870), 171. Ladenburg, Ann., 173 (1874), 162. Michaelis, Ann., 201 (1880), 247. Michaelis and Becker, Ber., 15 (1882), 185. Michaelis, Ann., 242 (1887). 180. Michaelis, Ber., 27 (1894), 247. Michaelis, Bey., 28 (1895), ,588; Zeiser, Ibid., 1670. Michaelis, A n n . , 293 (1896), 291. Willgerodt, Bcr., 31 (1898), 917; Bamberger and Kunz, Ibid., 1528. Dimroth. Ber., 32 (1899), 761. Michaelis, Ann., 315 (1901), 38. Dimroth, Chem. Zentr., [I] 1901, 451. “Habilitatiousschrift Tiibingen 1900.” Hilpert and Griittner, Ber., 48 (1915), 906; Chem. Abs., 9 (1915), 2251. Benzyl Compounds. Dreher and Otto, Ann., 154 (1870), 175; Z . Chem., 5 (1870). 19. Otto, J. prakt. Chem., 1 (18701, 184. Pope and Gibson, J. Chem. Soc., 101 (1912), 735. Wolff, Ber., 46 (1913), 64; Pope, Ibid., 352. Hi1pe;t and Grtittuer, Ber., 48 (1915). 910; Chem. Abs., 9 (1915), 2251. .,I 1%’. Jones, J. A m . Chem. S O L , 40 (1918), 1266.

MESITYLENE : .Michaelis and Sonnenkolb, Ber., 28 (1895). 591. CYMENE: Paterno and Colombo, Gam. chim. ital., 7 (1877), 421; Ber., 10 (1877), 1749. Michaelis and Sonnenkolb, Ber., 28 (1895), 592. PENTAMETHYL BENZENB: Jacobsen, Ber., 22 (1889), 1220. Mercury Derivatives of Aromatic Nitro Compounds I1 G, p. 80. NITROBENZENE: Dimroth, ‘Be?., 35 (1902), 2036. NITROTOLUGNES: Reissert, Ber., 40 (1907), 4209. See under Amines, Phenols, Acids, Etc Mercury Derivatives of Sulfinic and Sulfonic Acids I11 A and B, p. 108. SULFINIC ACIDS: Peters, Ber., 38 (1905). 2567. SULFONIC ACIDS: Dimroth, Chem. Zentr., [I] 1901, 454., Schoeller and Schrauth, Chem. Zentr., [I] 1910, 1079; Ger. Pat. 219,967. See under Amines, Phenols, Acids, Ete. SULFONYL CHLORIDES: Otto, Be*., 18 (1885), 247

Hilpert and Grtittner, Ber., 45 (1912), 2828. Cambi, Atli accad. Lincei, [ 5 ] 21 (1912), [ I ] 773; Chem. Z e n t r . , [II] 1912, 822. Hilpert and Grtittner, Ber., 46 (1913), 1675. Hilpert and Griittner, Ber., 48 (1915), 910; Chem. Abs., 9 (1915), 2251. L. W. Jones, J. A m . Chem. Soc., 40 (19181, 1268.

K o v . , 1919

T H E J O C R N . 4 L O F I1VDCSTRt.4 L A N D E N G I N E E R I N G C H E M I S T R Y

Mercury Derivatives of Higher Aromatic Hydrocarbons I V B, etc., p. 173. P H E N Y L ACETYLENE:

Nef, A n n . , 308 (1899), 298. Manchot and Haas, Ann., 399 (1913), 133. ~YAPHTHAI,ENE : Otto, Ann., 147 (1868), 164. Otto, J.p r a k t . Chem., [2] 1 (1870), 185. Otto, Z . Chem., 6 (1870), 23. . Otto, A n n . , 154 (1870), 188. Heuniann and Kbchlin, Be?., 16 (18831,

11627. Michaelis, B e y . , 27 (1894), 249 (alpha), 251 (heed). Chatlaway, J . Chem. Soc., 65 (1894), 878 Willgerodt, Bev., 31 (1898), 920. Dimroth, Chem. Zentr., [I] 1901, 454. Dimroth, Ber.. 35 (1902), 2035. Chem. Zentr., [I] 1914, 1720; Ger. P a t

.272,605. See Naphthylamines, Naphthols, etc. : Sand, A n n . , 329 (1903), 147. BIPHENYL: Michaelis, Ber., 28 (1895), 592.

%)IHYDRONAPIITHALENE

-Mercury Derivatives of Aromatic Amines ANILIN: V A, p , 308. Hofniann. A n n . , 47 (18431,62. Schiff, Compt. verzd., 56 (1863), 491. Forst.er, Ber., 7 (1874), 294. Rudolph, Ber., 11 (1878). 78. Klein, B w . , 11 (1878). 743. Klein, Bet'., 13 (1880), 834. Andre, Compt. rend., 112 (18911,995. Pesci, Atti accad. Lincei, [SI 1 (1892), 312; C h e m . Zenlr., [II]1892, 213. Pesci, Gaze. chim. ital., [I]22 (1892), 373. Piccinini and RcspaJgiari (Peici), Guzz chim i t a t . , [2]22 (1892), 608. Pesci, GQZZ.chim. ital., [I) 27 (1597), 567; C h c m . Zentr., [II]i897,482. Pesci, Z . anovg. Chsm., 15 (1877), 213. Montecchi (Pesci), Gam. chim. ital., [2] 28

(1898), 434; Chem. Zentr., [I]1899,381. Pesci, Gazz. chim. ital., [2] 28 (1898), 443; ,Chem. Zcntr., [I] 1899, 362. Dimroth, Bev., 35 (1902), 20327. Pesci, Z. anorg. Chem., 32 (1902). 227. Dimroth, Z . anorg. Chem., 33 (1903), 311. Fransois, J . p h a r m . chim., 6 (1906), 21. Schoeller and Schrauth, Chem. Zentv., '[I]1910, 1079;Ger. P a t . 219,967. Staronka, A k a d . Wiss. Krakau, [A] 1910, -672;Chem. Z e n f r . , [II]1910,1741. Reitzenstein and Stamm, J . p r a k t . Chem., [2]81 (1'$00),150. Reitzenstein, J . prakl. Chem., (21 86 (1912), 73. Vechiotti, Gaze. chim. ital., [2]144 (1914), 34;C k e m . Zentr., [II]1914,1350. Pearce and Fry, J Phys. Clzem., 18 (1914), 667. Jacobs and Heidelberger, J . Biol. Chem., 20 (1915), 513; Chem. Zentr., [II] 1915,g594; Chem. Abs., 9 (1915), 1609. METHYLANILINE: Pesci, Atti accad. Lincei, [5]2 1 (1892), 431; Chem. Zentv., [II] 1892, 522 Pesci, Gasz. chim. ital., [2] 22 (1892), 32; Chem. Zsntr., [II] 1893, 571. Pesci, Z nnorg. Chem., 15 (1897), 216. DIMETHYL ANILINE: Klein, B e y . , 11 (1878), 743,1741. Michaelis and Schenck, Ber., 21 (1888), 1501; A n n . , 260 (1890), 6 . Michaelis and Rahinerson, B e y . , 23 (1890),

2342. P e s 4 Gam. chim. ital., [2] 22 (1892), 32; Atti accad. Lincei, [SI 21 (1892), 433; Chem. Zenlr., [I]1893, 571.

Pesci, Gaza. chim. ital., [2] 23 (1893), 521; Chem Zentr , [I]1894,501. Pesci, Gazz. chim. i t d , [2]24 (1894). 462; Chcm. Zenlv., [I] 1895,334. Pesci, Z . anorg. Chem.. 16 (1897), 217. Pesci, Gazz. chim. ital., [2] 28 (1898), 441; Chem. Zentr., [I]1899,362. Dimroth, B e y . , 35 (1902),2044. Dimroth, Z. anovg. Chem., 33 (1903), 314. ETHYL ANILINE: Ruspaggiari (Pesci), Gazz. chim. i t d , [21 23 (1893), 544; Chem. Zentr., [I] 1894, 501. Pesci, Z . anorg. Chem., 15 (18971,219. D I E T H ~ ANILINE L : Piccinini (Pesci), Gazz. chim. ital., [21 23 (1893), 534; Chem. Zentr., [I] 1894, 501. Pigorini (Pesci), Gazz. chim. ital., [21 24 (1894), 465;Chem. Zentr., [I]1895,334. Pesci,' Z. anovg. Chem., 15 (1897), 220. ACETANILIDE : Oppenheim and Pfaff, Ber., 7 (1874), 624. Pesci, Gazz. chim. ital.,[21 24 (1894),449; Chem. Zentv., [I] 1895, 334; Chem. Zfg.,23 (1899), 5 8 ; Chem. Zentr., [I] 1899, 527. Pesci, Z . anorg. Chem., 15 (1897), 222. Pesci, GWZ. chim. itel., [2] 28 (1898), 457; Chem. Zentr., [I] 1899, 362. DIPHENYLANINE: Klein, Ber., 11 (1878), 743. Prussia (Pesci), Gazz. chim. ital., [2]28 (1898), 129,454;Chem. Zentr., [II]1898,928. METHYLDIPHENYLAMINE: Garbarini (Pesci), Gam. chim. itaZ., [2] 28 (1898), 133,456;Chem. Zentv., [II]1898,928. PHENYLGLYCINE: Schrauth and Schoeller, Bev., 44 (1911), 1300. Schoeller and Schrauth, Z . Hyg. Infekt.Krankh., 70 (1911),24;Chem. Zentv., [I]1912,596. Schoeller and Schrauth, Chem. Zenlr., [II] 1912, 211; Ger. Pat. 248,291. Chem. Zentr., [I] 1914, 1469: Ger. P a t . 272,289.

TOLUIDINES : Klein, (ortho and para), Bey., 11 (1878),

743, 744. Klein, Be?., 13 (1870), 835. Pesci (para), Gam. chim. ital., [2]28 (1898),

111. Chem. Zenlr., [I] 1910, 1079; Ger 219,967.

Pat,

Schrauth and Schoeller (ortho and meta), B w . , 45 (1912), 2809, 2812. Vecchiotti, Gazz. chim. ital., [II] 48 (1918), 78;Chem. Abs., 13 (1919), 1450. DIMETHYL TOLUIDINE: Pesci, Gazc. chim. ital., [2] 28 (1898), 101, 437;Chem. Zentr., [II]1898, 546. Pesci, Z . anorg. Chem.. 17 (1898), 276. ACETTOLUIDIDES : Schoeller and Schrauth, Rer., 45 (1912),

2813. ACIDS: Be?., 45 (1912), 2814. BENZYLAMINE: Pesci, GQZZ.chim. ital., [2] 26 (1896), 54; Chem. Zentr., [I11 1896, 630; Pesci, Z . anorg. Chem., 15 (1897), 221. BENZYLANILINE: Pesci, Gazz. chim. i t d , [ I ] 27 (1897), 13; z. anovg. Chem., 15 (1898), 221; Gasz. chim. itel., [2]28 (1898),453. METANILICACID: Chem Zentv., [I] 1915,73;Ger. P a t 281,009. AMINOPHENYLARSONICACIDS: Chem. Zentr., [I11 1911, 1398; Ger. Pat.

TOLUIDOACE'CIC

239,557. 'Summaries of the work of Pesci and his students may be found in Gazz. chim. ital., [2] 28 (1898),436,and Z. anorg. Chem., 15 (1897),

208; 17 (18981,276.

1087

NAPHTHYLAMINES : V D, p. 591. Klein, Ber., 11 (1878), 743. Prussia, Gazz chim. itd., [Z]28 (1898), 127; Gazz. chim. ital.,[2] 28 (1898), 459;Chem.

Zentr., [II] 1898, 928. Brieger and Schulemann, J . p r a k t . Chem.,

89 (1914), 140. NAPHTHYLAMINE SULFONIC ACIDS: Brieger and Schulemann, J . p r a k t . Chem..

89 (1914),110,124,127,142. Mercury Derivatives of Phenols VI B, p. 648. PHENOL: Desesquelles, Bull., [3] 11 (18941, 267. Dimroth, Ber., 31 (1898), 2155. Dimroth, Bey., 32 (1899), 76. Grutzner, Arch. Phwm., 236 (1899), 622; Chem. Zentr., [l]1899,203. Dimroth, Chem. Zentr., [I] 1901,451. Dimroth, Ber., 35 (1902), 2859. Schoeller and Schrauth, Chem. Zentr., [I] 1910, 1079;Ger. P a t . 219,967. Chem. Zentv., [I] 1914, 1720; Ger. P a t .

272,605. Chem. Abs., 10 (1916), 1694; Ger. P a t . 286,977. Schoeller and Schrauth, Chem. Abs., 11 (1917), 2916. ANISOL: Michaelis and Rabin-rson, Be?., 23 (1890),

2343. Michaelis, Ber., 27 (1894), 254. Michaelis, Ann., 293 (1896), 248. Lbloff, Ber., 30 (1897). 2836. DimrotW, B e y . , 35 (1902), 2867. PHENETOL: Michaelis, Ber., 27 (1894), 258. Michaelis, Ann., 293 (1896), 257. Loloff, Be?., 30 (1897), 2841. Dimroth, Be?., 32 (1899), 764. Dimroth, Chem. Zentv., [I] 1901,453. Dimroth, Bev., 35 (1902), 2867. PHENOXYLACETIC ACID: Chem. A b s . , 7 (1913), 4046; U. S. P a t .

1,074,781. HALOGEN PHENOLS: Chem. Zentr., [I] 1911, 1769; Ger. Pat.

234,851. Schrauth and Schoeller, Z . Hyg. Infekt.Kranizh., 82 (1916), 276;Chem. Abs., 11 (1917), 2916. Hantzsch and Auld, Ber., 39 (1906), 1117. NITROPHENOLS : Hantzsch and Auld, Ber., 39 (1906), 1105. Chem. Zentr., [I] 1911; 1769; Ger. Pat. 234351. HALOGEN NI'CROPHENOLS: Chem. Zentr., [I] 1911, 1769; Ger. Pat. 234,851. AMINOPHENOLS: Launoy and Levaditi, Compt. rend. soc. biol., 74 (1913), 18; Chem. Abs., 7 (1913), 1384. Fourneau and Vila, J . pharm. chim., 6 (19131,433; Chem. Abs., 7 (1913), 2286. ETHYLAMINO PHENOL: Chem. Zentr., [II] 1914, 1334; Ger. Pat. 279,957. ANISIDINE : See Methacetin. METHACETIN : Prussia, Gazz. chim. ital., (21 28 (1898), 123. MISCELLANEOUS PHENOXY COMPOUNDS: Launoy and Levaditi, Compt. rend., 153 (19111,1520; Chem. Zentr., [I] 1912, 598. Chem. Zentr., [II] 1913, 193; Ger. P a t ,

261,229. CRESOLS: Dimroth, Chem. Zentr , [I] 1901,453. Dimroth, B e r . , 35 (1902), 2856.

1088

T H E J O U R N A L 0'F I N D U S T R I A L A N D E N G I N E E R ' N G C H E M I S T R Y

Schoeller and Schrauth, Chem. Zentr., [I] 1910, 1079; Ger. Pat. 219,967. Bayer & Co., Chcm. Abs., 6 (1912), 1547; Brit. Pat. 24,981. XYLENOLS: Bayer & Co., Chem. Zenlr., [II] 1912, 1245; Ger. Pat. 250,746. Taub, Chem. Abs., 7 (1913), 3819; U. S. Pat. 1,073,942. : CARVACROL Chem. Zentr., [II] 1913, 193; Ger. Pat. 261,229.

THYMOL: Dimroth, Bey., 35 (1902), 2864. Chem. Zentr., [II] 1913, 193; Ger. Pat. 261,229; Ibid., 395; Ger. Pat. 261,875 Chem. Abs., 12 (1918), 739.

THIOPHENOL:

VI c, p. 779. Dreher and Otto, Ann., 154 (18701, 178. Lacher, Ber., 48 (191.5), 1425; Chem. Abs., 9 (1915), 3241. PHENOL SULFONIC ACIDS: VI D, p. 829. Lumiere, Compt. rend., 132 (1901), 145; Ckem. Zentr., [I] 1901. 455. Schoeller a n d Schrauth, Chem. Zentr.. [I] 1910, 217; Ger. Pat. 216,828. Schrauth, Seifensieder-Ztg., 37 (1910), 1276, 1323; Chem. Zentr., [I] 1911, 695. Rupp and Herrmann, Arch. Pharm., 254 (1917), 500; Chem. Abs., 11 (1917), 2713. HALOGEN PHENOL SULFONIC ACIDS' See Sozoiodol.

SOZOIODOL: Trommsdorf, Chem. Zentr., [I] 1912, 1521; Chem. Abs., 6 (1912), 2495; Ger. Pat. 245,534. Rupp and Herrmann, Arch. Phorm., 254 (1917), 488; Chem. Abs., [I11 11 (19171, 2713. AMINOPHENOL SULFONIC ACIDS: Chem. Zentr., [I] 1915, 73; Ger. Pat. 281,009. CRESOLARSONICACIDS: Chem. Zentr., [I] 1913, 353; Ger. Pat. 255,030. ANETHOLE : Balbiano, Atti accad. Lincei, [SI 11 [I11 (1902). 65; Chem. Zentr., [II] I902, 844. Balbiano and Nardacci, Gam. chim. dol., [I] 36 (1906), 256; Chem. Zentr., [II] 1906, 120. NAPHTHOLS: VI G . p. 856. Desesquelles, Bull. soc. chim., [3] 11(1894), 264. . Bamberger, Ber., 31 (1899), 2624. Bayer & C o , Chem. Ab$., 6 (19121, 1547; Brit. Pat. 24,981. Briege and Schulemann, J. prakt. C h e m , 89 (1914), 132. NAPHTHOXYL FATTY ACIDS: Chem Zentr., [II] 1913, 193; Ger. P a t 261,229. SULFONIC ACIDS: NAPHTHOL Chem. Zentr , [II] 1903, 403; Get Pat. 143.448; Ibid., 474; Ger. Pat. 143,726 Chem. Zentr., [I] 1913,353; Ger. Pat. 255,030. Briege and Schulemann, J. prakt Chem., 89 (1914), 105, 124, 136, 175. AMIDO NAPHTHOL SULFONICACIDS: J. prakt C h e m , 89 (1914), 155, 174. : PYROCATECHIN VI1 C, p. 907. Bayer & Co., Chem. Abs., 6 (1912), 1547, Brit. Pat. 24,981. Bayer & Co., Chem. Zentr., [II] 1913, 1183; Ger. Pat 264,267. GUAIACOL: Chem. Abs., 6 (1912). 1547. Chem. Zenlr., [II] 1913, 193; Ger. Pat. 26 1,229. : RESORCIN Dimroth, Ber., 35 (1903, 2865.

Vol.

11,

No. 1 1

SAFROL AND ISOSAFROL: VI1 D, p. 974. Balbiano, Atti accad. Lincei, [SI 11 [ I I ] (1902), 65; Chem. Zentr., [II] 1902, 843. Balbiano and Nardacci, Gaze. chim. ital., [l] 36 (1906), 268; Chem. Zenlr., [II] 1906, 120.

Chem. Zentr., 1111 1912, 1413; Ger. Pat. 251,332. Blumenthal and Oppenheim, B i o c h m . Z., 57 (19131, 261; Chem. Zentr., [I] 1914, 137. Blumenthal, 2. Immmitllt. [I] 20, 378; Chem. Zentr., [I] 1914, 481.

METHYLEUGENOL:

AMINOBENZOIC ACIDS: Friedlander, Ber., 15 (1882), 2106. Launoy and Levaditi, Compt. rend., 153 (1911), 1520. Blumenthal, Biochem. Z . , 32 (191 l ) , 59; Chem. Abs., 5 (1911), 3594. Schoeller and Schrauth, Chem. Zentr., [I] 1911, 1566; Ger. P a t . 234,054. Blumenthal, Deut. Med. Wochschr., 38 (1912), 543; Chem. Abs., 6 (1912), 1466; Chem. Abs., 6 (1912), 3165; Ger. Pat. 249,725. Schoeller and Schrauth, Chem. Zenlr.. [II] 1912, 211; Ger. Pat. 248,291. Blumenthal and Oppenheim, Biochem. Z., 39 (1912), 50; Chem. Zentr., [I] 1912, 1631. Blumenthal and Oppenheim, Biochem. Z., 57 (1913), 261; Chem. Zenlr., [I] 1914, 137. Blumenthal, 2. Immunital., [I] 20, 378; Chem. Zentr., [I] 1914, 481. Schoeller, B w . , 47 (1914), 1930. E. Forster, Monograph published by E. Ebering, Dresden.

Ibid. METHYL CHAVICOL:

Ibid. ASARON:

Ibid. APIOL AND ISOAPIOL: Balhiano and Nardacci, Gam. chim. ital., [I] 36 (1906), 256; Chem. Zentu., [I11 1906, 120. : CHOLESTEROL XI11 B, p. 1071. Simonelli, Rass. clin. terapia. sci. a f f i n i , 14 (1915). 329; Chem. Abs., 10 (1916), 951. Mercury Derivatives of Aromatic Acids BENZOICACIDS: XXIII D. p. 1136. Michaelis and Sonnenkolb, Ber., 28 (1893, 593. Pesci, Atti accad. Lincei, [SI 9 [I] (1900), 25.5; Chem. Zentr., [I], 1900, 1097. Dimroth, Chem. Zenlr., [II] 1901, 454. Pesci, Atti accad. Lincei, [SI 10 [I], 413; Chem. Zentr., [I] 1901, 108; J . Chem. Soc., 80 (1901), 624. Michaelis, Ann., 315 (1901), 35. Dimroth, Ber., 35 (1902), 2870. Pesci, Gam. chim. ital., [2] 32, 277; Chem. Zentr., [II] 1902, 1454. Schoeller and Schrauth, Z . H y g . Infekt.Rrankh., 66 (1910), 497; Chem. Zentr., [I11 1910, 1395; Chem. Abs., 5 (1910), 1816. Schoeller and Schrauth, Chem. Zentr., [I] 1910, 1767; Ger. Pat. 221,483. Schoeller and Schrauth, Biochem. Z., 33 (1911), 38; Chem. Zenlr., [I11 1911, 707. Schoeller and Schrauth, Chem. Zenlr., [I] 1911, 1566; Ger. Pat. 234,054. Devillers, Bull. sci. pharmacolog., 18 (1913), 639; Chem. Abs., 7 (1913), 1580. Chem. Zentr., [11] 1913, 39.5; Ger. Pet. 261,875. Chem. Abs., 12 (1918), 1495. BENZAMIDB: Dessaigines, A n n . , 82 (1852), 234. Oppenheim and Czarnowsky, Bw., 6 (1873), 1392. Tafel and Enoch, Bey., 23 (1890), 1553. Rieseritzky, 2. physik. Chem., 28 (1899), 399.

DIBENZHYDRA~IDE: Stoll6, Ber., 45 (1912), 273. HIPPURICACID: Ibid., 391. HALOGEN BENZOICACIDS: Bayer & Co., Chem. Abs., 5 (1911), 3127; Brit. P a t . 28,049. Chem. Zentu., [I] 1911, 276; Ger. Pat. 229,574. Schoeller and Schrauth, Chem. Zentr., [I] 1911. 1566; Ger. Pat. 234,054. Bayer & Co., Chem. Zentr.. [II] 1911, 112; Ger. Pat. 234,914. Schoeller and Schrauth, Biochem. Z., 33 (1911), 381; Chem. Zenlr., [I11 1911, 707. Bayer & Co., Chem. Zentu.. [I11 1912, 465; Ger. Pat. 249,332. NITROBENZOIC ACIDS: Blumenthal, Biochem. Z., 32 (1911), 59; Chem. Abs., 5 (1911). 3594. Blumenthal, Deut. Med. Wochschr., 38 (1912), 543; Chem. Abs., 6 (1912), 1466. Chem. Abs., 6 (1912). 3165; Ger. Pat. 249,725. Biochem. Z., 39 (1913, 50; Chem. Zentr., [JJ 1912, 1631.

SULFAMIDOBENZOIC ACID: Chem. Abs., 6 (1912), 2146; Chem. Zen&., [II] 1912, 166; Ger. Pat. 242,571. Chem. Abs., 7 (1913), 867; Ger. Pat. 242,572. Chem. Zenlr., [I] 1915, 73; Ger. Pat. 281,009.

1

METHYLBENZOICACIDS. TOLUIC ACIDS: Schoeller and Schrauth, Chem. Zenlr., 111 1911, 1566; Ger. Pat. 234,054. Bayer & Co., Chem. Zetllr., [II] 1911, 112; Ger. P a t . 234,914; Brit. Pat. 28,049. Z . Hyg. Infekt.- Krankh., 77 (1914), 436; Chem. Zentr., [I] 1915, 562. TRI-METHYLBENZOICACIDS: Bayer & Co., Chem. Zentr., [II] 1912, 465;. Ger. Pat. 249,332. Taub, Chem. Abs., 6 (1912), 2674; U. 9. Pat. 1,034,166. CINNAMICACID: XXIII E, p. 1404. Biilmann, Bey., 35 (1902), 2571. Biilmann, Bey., 41 (1908), 4340. Biilmann, Ber., 43 (1910), 573. Schrauth and Schoeller, Ber., 43 (1910), 695. Schrauth and Schoeller, Ber., & ( I Q l l ) , . 1048, 1432. Schrauth and Schoeller, Chem. Abs., 5. (1911), 2307, 3127; Chem. Zentr., [I] 1911, 102; Brit. P a t . 27,049; Ger. P a t . 228,877. PHENYL PROPIOLICACID: XXIII F, p. 1438. Schrauth and Schoeller, B w . , 44 (1911),. 1057. OXYBENZOIC ACIDS, SALICYLIC ACID: XXIV D. p. 1488. Lajoux, J phorm. chim., [SI 5 (laso), 39. Balestra, Case. chim. ital., [2] 22 (18929,. 568; Chem. Zentr., [I] 1893, 559. Lajoux and Grandval, Compt. rend., 117 (1893) 44. Dimroth, Bey., 35 (1902), 2033, 2872. Buroni, Gaaa. chim. ita!., [2] 32 (1902), 305;. Chem. Zentv., [I] 1903, 578. Schoeller and Schrauth, Chem. Zentr., [13. 1910, 1078-9; Ger. Pats, 219,966 and 219,9672. Chem. Abs., 5 (1911), 1661; Fr. Pat. 404,491. Chem. Zentu., [I] 1911, 1266. G ~ F . Pat. 233,437. Brieger, Arch. Pharm., 250 (1912), 6 2 ; . Chem. Zentr., [I] 1912, 753. Blumenthal, Biochem. Z . , 39 (1912), SO;. Chem. Zentr., [I] 1912, 1631. Chem. Zentr., [II] 1912, 166; Ger. Pat.. 247,625. DI-

AND

Nov., 1919

T H E J O U R N A L OF I N D U S T R I A L A N D E N G I N E E R I N G C H E M I S T R Y

Schoeller and Schrauth, Chem. Zentr., [ I n 1912, 21 1; Ger. Pat. 248,291. Chem. Zentr., [I] 1913, 353;

Ger. Pat.

255,030.

Chcm. Zentr., [II] 1913, 193; Ger. Pat. 261,229. Gadamer, Arch. Pharm., 256 (1918), 263; Chcm. Abs., 13 (1919), 1364. ACID DOUBLECOMPOUNDS WITH AMINO ACIDS,ETC.: Buchtala, Z . ghysiol. Chem., 83 (1913), 280, 283. Scboeller and Schrauth, Therap. Monatsh., 23 (1909), 4; Chem. Zentr., [I1 1910, 948. Chem. Zentr., [I11 1910, 609; Chem. Abs., 5 (1911), 156; Ger. Pat. 224,435. Cham. Zentr., [II] 1910, 701; Ger. P a t . 224,864. Chem. Zentr., [I11 1910, 1423; Chem. Abs., 5 (1911), 2154; Ger. Pat. 227,391. Engelmann, Chem. Abs., 5 (1911), 971; U. S. Pat. 978,145. Bayer & Co., Chem. Abs., 5 (1911), 3880; U.S. P a t . 1,001,829. Schoeller and Schrauth, Biochem. Z . , 33 (1911), 381; Chem. Zentr., [II] 1911, 707. Chem. Zentu., [I] 1911, 275-6; Ger. Pats. 229,574, 229,575, 229,781. Buchtala, Z . ghysiol. Chem., 83 (1913), 249. Blumenthal, Biochem. Z . , 57 (1913), 261; Cbem. Zentr., [I] 1914, 137.

SALICYLIC

Schmidt, Pharm. Z . , 60 (1916), 724; Chem. Abs., 10 (1916), 951. META-A N D PARA-OXYBENZOIC ACIDS: Chem. Zentr., [I] 1911, 276; Ger. Pat. 229,575. Engelmann, Chem. Abs., 6 (1912), 2674; U. S. P a t . 1,034,092. Blumenthal, 2. Inamunitat., [I] 20 (19141, 3 7 8 ; Chem. Zentr., [I] 1914, 481. SALICYLAMIDE : Kieseritzky, 2. physik. Chem., 28 (1899), 393. SULFOSALICYLIC ACIDS: Schrauth and Schoeller, Biochem. Z., 33 (1911), 381; Chem. Zentr., [II] 1911, 707. Chem. Zentv., [I] 1913, 353; Ger. Pat. 255,030. Blumenthal and Oppeuheim, Biochem. Z . , 57 (1913), 261; Chem. Zentr., [I] 1914, 137.

SALICYL ARSONICACIDS: Chem. Zentr., [I] 1913, 353; Ger. Pat. 255,030.

1089

TYROSIN: Chem. Zentr., [11] 1914, 1334; Ger. Pat. 279,957.

Chem. Abs., 10 (1916), 1578; Holl. Pat. 1,179. Buchtala, Chem Abs., 10 (1916), 1693; U. S. P a t . 1,180,694. Buchtala, Chem. Abs., 12 (1918), 1909; U. S. Pat. 1,271,846. AMINOPHENYLGLYOXYLIC ACID: Peters, Ber., 40 (1907), 237.

ISATIN : XXIV E, p. 1601. Peters, Ber., 40 (1907), 235. OXYNAPHTIIOIC ACIDS XXIV a,p. 1687. Brieger and Schulemann, J. prakt. Chem., [2] 89 (1914), 176, 179. OXYSULFONAPHTHOIC ACIDS: J . prakt. Chem., [2] 89 (1914), 182.

PHTHALIMIDE: XXV E, p. 1798. Landsberg, Ann., 215 (1882), 189. Kieseritzky, 2.ghysdk. Chem., 28 (1899), 402.

METHOXYBENZOICACIDS. ANISIC ACID: Schrauth and Schoeller, Chem. Zentr., [I] 1911, 1566; Ger. Pat. 234,054.

FLUORESCEIN : XXVIII I, p. 2060.

DIMETHOXY BENZOICACID: Bayer & Co., Chem. Zentr., [I11 1912, 465; Ger. Pat. 249,332.

1908, 1307; Ger. Pat. 201,903; see Friedlander, 9, 1071. Chem Abs., 12 (1918), 2015.

Pauly and Traumann, Chem. Zentr., [II]

SECTION 3 Mercury Derivatives of Aromatic Ketones ACSTOPHENONE: VI C, p. 118. Michaelis, B w . , 28 (1893, 593. Dimroth, Ber., 35 (1902), 2869 Grignard and Abelman, Bull. SOC. chim., 141 19 (1916), 1525; Chem. A b s , 10 (19161, 1525. : BENZOPHENONE VI G, p. 180. Dimroth, Ber., 35 (1902), 2868. Grignard and Abelmann, Bull. sac. c h i m , [4] 19 (1916), 1525; Chem Abs., 10 (1916), 1525. DIXETOHYDRINDENE : V I I C, p. 274. Peters, Ber., (1907), 239. Hantzsch, Ann., 392 (1912). 286. Mercury Derivatives of Terpenes Camphors XI B, p. 482.

CAMPHOR : Tafel a n d Schmitz, Z . Elektrochem., 8 (1902), 287. Marsh and Fleming-Struthers, Proc. Chem. Sac., 23 (1907), 246; 24 (1908), 267. Marsh and Fleming-Struthers, J. Chem. Sac., 95 (1909), 1777; 97 (1910), 2410. PINENE AND CAMPHENE: Balbiano, Atti accad. Lincei, [5] 11 [11] (1902), 65; Chem. Zentr., [11] 1902, 843. Balbiano and Paolini, Ber., 35 (1902), 2995; 36 (1903), 3576. Balbiano, Gazz. chim. ital., [I] 36 (1906), 301; Chem. Zentr., [I11 1906, 126,

TERPIN: and

TERPINEOL AND TERPIN: Sand and Singer, Em., 35 (19021, 3170. Sand, A n n . , 329 (1903), 142.

See above with “Terpineol.” Mercury Derivatives of Thiophene Compounds THIOPHENE : XXI A, p. 738. Volhard, A n n . , 267 (1892), 172.

DenigBs, Compt. rend., 120 (1895), 6 2 8 , 781. DenigBs, Bull. soc. chim., [31 13 (l895), 537; 15 (1896), 1064. Dimroth, Ber.. 32 (1899), 759; 35 (1902). 2035. Schwalbe, Ber., 38 (1905), 2298. Steinkopf and Bauermeister, Ann., 403 (1914), 15, 50. Steinkopf, A n n . , 413 (1917), 310; Chem. Abs., 11 (1917), 2326. ALKYLAND HALOGEN THIOPHENES: Ibid.

THIENONE : Volhard. Ann.; 267 (1892), 172. Mercury Derivatives of Alkaloids1 XXV, p. 772. I-Iinterberger, Ann., 77 (1851), 201; 82 (1852), 311. Ray, J. Chem. Sac., 111 (1917), 507. ‘See also under the individual Alkaloids Beil., 3rd Ed., 3, pp. 770-967.

SECTION 4 Mercury Derivatives Compounds

of

Organic

Nitrogen

PIPERIDINE : I A, p. 3. Ccrdeili (Pesci), Z . anmg. Chcm., 15 (18971, 213; Gasz. chim. ital., [ l ] 27 (1897), 18; Ibid., [2] 28 (1898), 473. ‘hIA2OLE :

I C, p. 63. Dohle and Rassow, 2. Chem. Ind. Kolloids, 12 (1913), 71; Chem. Abs., 7 (1913), 3320. PYRIDINE:

I D, p. 104. Pcaci, Gaea. chim. ital.. [21 25 (1895). 423; Chem. Zentr., [I] 1896, 443; 2. anorg. Chem., 19 (1897), 228. Stromholm, 2. anorg. Chem., 57 (1908), 101 Staronka, Akad. Wiss. Krakau, [A] 1910, 372; Chem Zentr., [II] 1910, 1741. Reitzenstein and Stamm, J. 97akt. Chem., [2] 81 (1910), 150. Mathews, J. Phys. Chem., 21 (1917), 269; C h r a . Abs., 11 (1917). 1924.

PICOLINE: Pesci, Gam. chim. dtal., [ l ] 27 (1897). 23; 2. anorg. Chem., 15 (1897), 229; Gazz. chim. ital., [2] 28 (1898), 472. INDOLE :

I F. p. 216. Chem. Zentr., [II] 1911, 404-5; Ger. Pat. 236,893. QUINOLINE : I G, p. 247. Schiff, Compt. rend., 57 (1863), 837. Pesci, Gam. chim. ital., [ l ] 25 (1895), 394; Chcm. Zentr., [II] 1895, 225; Z . anorg. Chem., 15 (1897), 225; Gam. chim. itat., [2] 28 (1898), 467. Staronka. Akad. Wiss. Krakau, [A] 1910, 372; Chem. Zentr., [II] 1910, 1741. Chcm. Abs., 10 (1916), 2500; Ger. Pat. 289,246. ACRIDINE :

I K, p. 405. Chcm. Abs., 12 (1918), 1.259,S 17.

1496; U. S. Pat.

PYRAZOLONES : Chem. A b s , 6 (1900), 794; U. S. Pat. 1,016,784; Ibid., 6 (19001, 1500; Brit. Pat. 28,583. Kolle, Deut. med. Wochschtr., 3 8 (1912), 1582, Chem Zentr., [II] 1912, 1574. Chem. A b s , 7 (1913), 2995; U. S. Pat. 1,068,172. Schrauth and Bauerschmidt, Ber., 47 (1914), 2736 Chem. Abs., 13 (1919), 1126; Ger. Pat. 307,893. PHENYL HYDRAZINE:

Marsh and Fleming-Struthers,

J. Chum.

Sac., 87 (1905), 377.

PYRIMIDINES:

Chem. Abs., 5 (1911), 155; Ger. Pat. 224,491. QUINAZOLONES : Bogert, J . A m . Chem. SOC,34 (1912). 530.

SAFRANINES : Chem. Zentr.. I111 1915, 569; Chem. A k , 10 (1916), 1080; Get. Pat. 286,097.

1090

T H E JOURNAL.OF I N D U S T R I A L A N D ENGINEERING CHEMISTRY

CYCLO MERCURIPOLYMETHYLENES: Braun, Bey., 46 (1913), 1792. Hilpert and Grtittner, Ber , 47 (1914), 189. Braun, Ibid., 490. Azo COMPOUNDS: Smith, J. Chem. Soc., 93 (1908), 847; 95 (1909), 1435. Schamberg, Am. J. Syahilis, 1 (1917), 41; Chem. Abs., 11 (1917), 1690. P A R T 11-REACTIONS

1701.

11,

NO.

II

DIAZONIUM SALTS: Bamberger, Rev., 31 (1898), 2624. Dimroth, Bey., 35 (1902), 2034, 2859, 2863.

NUCLEICACIDS: Blumenthal, Biochem. Ztg., 57 (1913), 261; Chem. Zentr., [I] 1914, 137-8.

ALBUMEN: Chem. Abs., 6 227,391.

Reactions of Mercury Salts with Organic Antimony Compounds Michaelis and Reese, A n n . , 233 (1886). 49. Michaelis, Ann., 242 (1887), 170. Loloff, Ber., 30 (1897). 2836.

(1911), 2154; Ger.

Pat.

HAEMIN: Kobert, Apath. Ztg., 29 (1914), 887; Chem. Zentr., [II] 1914, 1447.

O F M E R C U R Y DIALKYLS, DIARYLS, A N D O R G A N 0 MERCURIC SALTS WITH T H E FOLLOWING CLASSES OF COMPOUNDS

ACID HALIDES: Heumann and Kiichlin, Ber., 16 (1883), 1626. Volhard, Ann., 267 (1892), 178. ACIDS: Buckton, A n n . , 112 (1859), 221. Schorlemmer, Ann., 132 (1864), 234. Otto, J. prakt. Chem., [2] 1 (1870), 179. Cahours, Compt. rend., 76 (1873), 748. Sand and Singer, Ber., 35 (1902), 3172. Wolff, Ber., 46 (1913), 65. Jones and Werner, J. A m . Chem. SOL, 40 {1918), 1257-1272. AMMONIA : Pesci, Gam. chim. i t d , [I] 39 147; Chem. Zentr , [I] 1909, 1092. ANTIMONY CHLORINE: Hasenbaumer, Ber , 31 (1898), 2911. : ARSENICCHLORIDE LaCoste and Michaelis, Ann., 201 (1880), 196, 247. PHENYLARSENICDICHLORIDE: LaCoste and Michaelis, Ann., 201 (1880), 238. BORONHALIDES: Michaelis, Bey., 13 (1880), 59. Michaelis, Ann., 315 (1901), 29. CHLOROBORMIC ESTER: Paterno and Colombo, Gam. chim. ilal., 7 (1877), 421; Ber., 10 (1877), 1749.

CYANOGEN CHLORIDE: Paterno and Colombo, Gam. chim ktal., 7 (1877). 421; Ber., 10 (1877), 1749.

ELECTROLYSIS IN LIQUID AMMONIA Kraus, J. Am. Chem. Soc., 35 (1913), 1732. GRIGNARD REAGENT: Hilpert and Grtittner, Bev., 48 (1915), 906; Chem. Abs., 9 (1915), 2251. Jones and Werner, J . A m . Chem. Soc., 40 (1918), 1266 HALOGENS: Buckton, A n n , , 112 (1859), 221. Otto, J. prakt. C h e m , [2] 1 (1870), 182. Sakurai, J. Chem. Soc, 39 (1881), 486.

Pesci, Gazz. chim. itaE., [2] 23 (1893), 526; Chem. Zentr., [I] 1894, 501. Sand, Ber., 34 (1901), 1388, 1391. Dimroth, Ber., 35 (1902), 2859, 2869, 2871, 2873. IODIDE CHLORIDES: Willgerodt, Be., 30 (1897), 56. Willgerodt, Ber., 31 (18981, 915. IODIDES : Pesci,' Gazz. chim. ital., [2] 23 (1893), 523; Chem. Zentr., [I] 1894, 501. Steinkopf, A n n . , 413 (1917), 310; Chem. Abs., '11 (1917), 2326. MERCURICSALTS: Otto, Ann., 147 (1868), 179. Otto, J. prakt. Chem., [21 1 (1870), 180. Steinkopf, A n n . , 413 (1917), 310; Chem. Abs., 11 (1917), 2327. METALS: Ruckton, Ann., 112 (1859), 223. Franklandand Duppa, A n n . , 130 (1864), 120. Cahours, Compt. ?end., 76 (1873), 134, 748, 1383; Ibid., 77 (1873), 1405. LLlhr, Ann., 261 (1891), 78. Fleck, Ann., 276 (1893), 138. Schorigin, Bey., 41 (1908), 2718. Schorigin, Ber., 43 (1910), 1931. Hilpert and Griittner, Rer., 45 (1912), 2829. Hilpert and Grtittner, Ber., 46 (1913), 1680. NITROUSACID AND ITSANHYDRIDE: Bamberger, Ber , 30 (1897), 507. Kunz, Ber., 31 (1898), 1528. Bamberger and MBller, Ber., 32 (1899). 3546. Dimroth, Ber., 35 (1902), 2856. OXIDIZINGAGENTS: Dreher and Otto, A n n . , 154 (1870), 125. Seidel, J. prukt. Chem., [2] 29 (1884), 134. PHOSPHOROUS CHLORIDE: Michaelis and K&hler, Ber., 9 (1876), 521 Michaelis, A n n . , 181 (1876), 280. Michaelis and Schenk, Ann., 260 (1890), 6. Michaelis, Ann., 293 (1896), 212. P A R T 111-MISCELLANEOUS

"Addition Compounds" of Organic Substances and Inorganic Compounds. (For exhaustive treatment of this subject see Gmelin-Kraut-Friedheim-Peters, Vol. V Part 11, pp. 876 t o 978.) ALKYLATION O F MERCURICAROMATICAMINES: Pesci and collaborators, Gasz. chim. ital., [2] 23 (1893), 523, 527, 531, 537; 121 28 (1898), 109; Chem. Zentr., [I] 1894, 501; [II] 1898, 546; Dimroth, Bey., 35 (1902), 2043. ANALYSIS : Ann., 130, 104; Bull. SOL. chim., [3] 15 ( 1896), 1064. Chem. Zentr., [II] 1911, 722; [I] 1912, 753; [11] 1912, 151; [IT] 1913, 1341. Chem. Abs., 7 (1913), 536, 896; 10 (1916), 1486 (C, H, and Hg), 1574, 2080; 1 1 (1917), 1258, 1385, 1517, 2080, 2136, 2211, 3292; 12 (1918). 659, 739, 740, 1395, 2072, 2180, J . Chem Soc., 103, 513; Z . anorg. Chem., 80, 212; 2. physiol. Chem, 83 (1913), 249.

TELLURIUM: Krafft and Lyons, Bev., 27 (1894), 1769. Zeiser, Ber., 28 (1895), 1670. SILICON CHLORIDE: Ladenberg, Ann., 173 (1874), 151, 165.

THIOSULFATES : Pesci, Gaze. chim. ital., [2] 28 (1898), 104, 112 132, 134; Chem. Zentr., 2 (18981, 546. Pesci, Gazz. chim. itul., [I] 29 (18991, 395; Chem. Zentr., 2 (1899), 481. Cimroth, Ber., 35 (1902), 2042. Pesci, Gazs. chim. ital., [I] 39 (1909), 147; Chem. Zentr., 1 (1909), 1092; Chem. Abs., 3 (1909), 1144.

TIN CHLORIDE: Aronheim, Ann., 194 (1878), 148. ZIRCONIUM CHLORIDE: Peters, Ber., 41 (1908), 3173.

TOPICS

ARSENIC COMPOUNDS CONTAININGMERCURY: Chem. Zentr., [II] 1911, 1398; [I] 1913, 353; [I] 1914, 1469; Chem. Abs., 10 (1916), 65; 11, 1690. See also G. T. Morgan, "Organic Compounds of Arsenic and Antimony," Longmans. DIAZOTIZATION OF MERCURIC AROMATIC AMINES: Jacobs and Heidelberger, J. B i d . Chem., 20 (1915), 513; Chem. Abs., 9 (1915), 1609. DIOLEFINES(?): Sand, A n n . . 329 (1903), 157. reference.)

REDUCINQAGENTS(ALKALINE) : Sand, Bey., 34 (1901), 1394, 2911, 2914. Dimroth, Ber., 35 (1902), 2034, 2854; I b i d . , 35 (1902), 3079. Chem. Abs., 6 (1912), 3165; Ger. P a t . 249,725. Chem. Zentr., [I11 1912, 1413. Ger. P a t . 251,332. Chem. Zentr., [I] 1913, 353; Ger. P a t . 255,032. SULFIDES (Na, K, AND METHYL): Pesci, Gazs. chim. ital., [2] 23 (1893), 525, 533; Piccinini, Ibid., 541. Raspuggiari, Ibid., 547; Chem. Zenlv., [I] 1894, 501. Pesci, Gam. chim. ital., [l] 29 (1899), 394; Chem. Zentr., [21 1839, 481. Pesci, G a m . chim. ital., 121 32 (1902); Chem. Zentr., [2] 1902, 1454. OTHERSULFUR COXPOUNDS: Otto, J . prakt. Chem., [2] 1 (1870), 183. Zeiser, Ber., 28 (1895), 1674. Pesci, Gazz. chim. %'tal,, [I] 39 (1909). 151; Chem. Zentr., [I] 1909, 1092. SELENIUM : Krafft and Lyons, Ber., 27 (1894), 1771. Zeiser, Ber., 28 (1895), 1671.

(Doubtful

DISINFECTING A N D ANTISEPTICACTION: Chem. Zentr., [II] 1897, 369; [II] 1910, 1395; [I] 1911, 1266; [II] 1911, 1877; [I] 1912, 596: [TI] 1913, 1421, 1709: [II] 1914, 1016. Chem. Abs., 5 (1911), 1816; 6 (1912), 1547, 1958; 10 (1916), 1677, 1694, 2492; 11 (1911), 2247, 2916; 12 (1912), 379,388, 1076, 1985, 2015. Z , physiol. Chem., 47, 173.

GRIGNARD REAGENT WITH MERCURY'COMPOUNDY: Ber., 37 1125; 46, 64, 352, 1675; 47, 178, 1651; 48, 905; Chem. Abs., 9 (1915), 2251. J. A m . Chem. Soc., 40, 1266; J. Chem. Soc., 101, 735. HEATINGMERCURY S A L T S O F ORGANIC ACIDS: Ber., 35, 2870. HETEROCYCLIC RINGS WITH MERCURYI N THE RING: Ber., 46, 1792; 47, 189, 490. MIXED MERCURYDIALKYLS, ETC.: Monatsh., 1 (ISSOj, 716; Ber., 456, 1675; 48, 906. : OXYMERCARBIDE Ann., 309, 171; Bey., 31, 1904; 33, 1328, 38, 3654. PHARMACOLOGY, PHYSIOLOGICAL ACTION, A N D TOXICITY OF ORGANICMERCURIALS: Chem. Zentr., [I] 1911, 1523: 1111 1911, 627, 707; [11] 1912,1224; [II] 1914, 1245; [I11 1915, 1275;

NOV.,

1919

T H E J O U R N A L OF I N D U S T R I A L A N D E N G I N E E R I N G C H E M I S T R Y

Chem. Abs., 5 (1911), 3080, 3594; 6 (1912), 1466, 14.70, 2262; 7 (1913), 152, 164, 168, 1054, 1234. 2066, 3365; 10 (1916), 496, 784, 809, 1220, 1555, 2005, 2481, 2937,,3105. Cht:m Abs., 11 (1917), 67, 171, 665, 848, 850, 1692, 1995, 2117, 2120, 2236, 2500, 2527, 3331; 12 (1918), 953, 1216, 1323, 2014, 2383, 2624. Z . physiol. Chem., 83, 249. PHYSICAL AND INORGANIC: A m . J . Sci., 35, 353; J. A m . Chem. Soc., 37 (1915), 70; 39 (1917), 948. Bev., 12, 563; 32, 1357; 33, 1010; 35, 1311; 38, 973; 39, 3626; 45, 1394. J. Phys. Chem., 9, 641; Chem. Zentr., [II] 1913, 324; [II] 1914, 1175; [I11 1915, 565. Chem. A b s . , 10, 570; 11, 1206, 2095, 3035. Comfit. rend., 129, 918; 154, 695; Gam. chim. dal., [ I ] 24, 311. J. Phys. Chem., 16, 261; J . Chem. Soc., 101, 1514; 103, 1550, 105, 658. Z. anorg. Chem., 82, 329; Z . physik. Chem., 13, 303; 27, 293; 28, 385; 34, 488; 36, 385; 42, 690; 59, 424; 69, 299; 86, 1 7 7 . “ P R O P R l l T A R Y ” ORGANIC MERCURIALS: AFRIDOL:

Chem. Zentr., [11] 1911, 1877; Z . angew. Chcm., 24 (1911), 677. ASUROL: Chem. Zentr., [I] 1910, 948. CONTRILLUESIN :

Chem. Abs., 7 (1913), 863.

EXBARIN :

SYPHILIS,TREATMENT WITH

Chem. Zentr., [I] 1914, 137.

ENESOL: Chem. Zentr., [I] 1914, 137; Chem. Abs., 10 (1916), 951.

HECTINE :

Chem. Abs., 5 (1911), 914. HYDRARGYROL :

Chem. A b s , 11 (1917), 2713. Chem. Zenlr., [I] 1915, 1275. MERCUROPHEN:

Chem. Abs., 11 (1917), 2247. : MERIODIN

Z . angew. Chem., 24 (1911), 678. No. 99 Same as Mercurophen. NOITOL :

Z . angew. Chem., 24 (1911), 678. PROVIDOL:

Chem. Abs., 11 (1917), 2916.

TOXYNON : Chem. Zentu., [I] 1914, 137. SOLUBLE MERCURY COMPOUNDS FROM ORGANIC MERCURIALS AND BASIC ORGANICSUBSTANCES : Chem. Zentr., 1 (1910), 948; 2 (1910), 609, 701, 1423; 1 (1911), 275, 276; 2 (1913), 1182. Chem. Abs., 5 (1911), 2154, 3880.

Chem. Zentr., [I] 1912, 598; [II] 1912, 1051-2, 1366.

1575;

[I]

1914.

137,

481,

804.

Chem. Abs., 6 (1912), 1034; 7 (19131, 151, 1384; 10 (19161, 640, 784; 1 1 (1917), 667, 825, 1690, 1992, 2233, 2235, 3334; 12 (1918), 186, 1567, 1797; 13, 1126. Compt. vend., 153, 304, 1520. MERCURY-MISCELLA-

NEOUS:

Ann., 146, 148; 241, 117; 359, 202; 371, 201; J. A m . Chem. Soc., 41, 777. Bull. soc. chim., [4] 9, 532; [41 17, 353. Chem. Zentr., [I] 1910, 1767; 1111 1911, 1 7 0 : Chem. Abs., 5 (1911), 3129; 9 (1915), 3241; 10 (1916), 2669. Chem. Ztg., 34, 89; Gam. chim. ital., [I] 29, 394; Chem Zentv., [II] 1899, 481. J . Chem. Soc., 111, 511. UNSATURATED

ACIDS,

ACTION

OF

MERCURIC

SALTS: Ber., 35, 2571; 41, 4340: 43, 568, 695; 44, 1048.

Chem. Abs., 5 (1911), 2307, 3127. UNSATURATED AND

COMPOUNDS,

PROPENYL

ACTION O F ALLYL

BENZENESWITH MBR-

CURIC ACETATE:

Ber., 35, 2995; 36, 3575; Chem. Zenlr., [II] 1902, 843; [II] 1906, 120, 126

EDITORIAL CORRESPONDENCE, AN ICEBERG LOOMS OUT OF THE FOG

ORGANIC MER-

CURIALS:

THIO COMPOUNDSOF

MERCINOL :

Unless our pilot, the Congress of the United States, steers a true course, one new ship of our industrial emergency fleet, the American dye industry, may go quickly to wreck upon an iceberg which looms suddenly out of the fog of these rapidly shifting times. I refer to the present greatly depreciated value of the German mark, the unit of currency in that land of dye manufacture, Safety from such a disastrous wreck lies alone in the enactment b y Congress of a strict license law for the control of importation of dyes from every country. I wish to give that message as wide circulation as possible through the columns of THISJOURNAL. It may be that the message is late; t h a t legislation of this character has already been enacted. If so, all is well. If not-then I hope that this letter may be of service to the members of Congress, who, I am confidont, are unanimously in favor of protecting this industry, so essential to our economic independence and so intimately bound up in the matter of our future national security. There have been, however, differences of opinion as to how best to accomplish this protection. M y sincere hope is that this recent. development may lead our representatives in Congress, Republicans and Democrats alike, to unite in unanimous support of a strict license system. The details of that system are of small importance in comparison with the fundamental and urgent importance of the general principle. Let me explain. At the time of the hearings on the Longworth bill before the Ways and Means Committee of the House of Representatives the rate of exchange with Germany was an unknown quantity and the subject never entered the discussions a t those protracted hearings. Soon after the signing of the Peace Treaty a t Versailles trading in German marks began. At first this trading was of a private character, but with the lifting of the blockade and the resumption of trade the rate of German exchange began to be quoted publicly, and showed a value of the mark from eight to ten cents, a great depreciation as compared with its pre-war value of a fraction over twenty-four cents. Gradually this rate

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has dropped, until to-day the mark is worth only four cents in American money. What significance has this depreciation for all who are interested in the permanence of the American dye industry? Simply this-if a certain dye sold in Germany before the war for, say, 6 marks per kilo, then $1.44 was paid for it by the importer. The same dye a t the same price now would cost the importer only 24 cents. Or, if cost of production in Germany has doubled during the war, it would still be only 48 cents, one-third of the pre-war cost. Can our manufacturers be expected a t the present time to compete with such conditions? T h e effect upon our customs duties would be also very marked, for a dye such as a vat dye, which pays 30 per cent ad valorem duty only, would now, because of the change in the rate of exchange, pay only one-sixth of the pre-war duty. It’s a pretty good argument for Mr. Fordney’s idea of assessing duties at the selling price in America instead of on invoice valuations. It also points clearly t o the fact that Mr. Longworth should raise the specific duty rates in his bill. The specific duties are based solely upon poundage, a standard which does not vary with the fortunes of war. If license legislation is not enacted, “dumping” of a perfectly legitimate character, which no anti-dumping law can reach, will abound and the young American dye industry will be prostrated, though i t has so splendidly done its part in carrying our consumers through the war period, though it bids fair to do away completely with the old evil practices of graft, bribery and other forms of commercial corruption, and though it offers an attractive field for a large number of young organic chemists and technically trained workmen who would constitute the chief reserve of our Chemical Warfare Service in times of conflict. Of course this rate of exchange will eventually approach normal pre-war rates, but the damage to our dye industry would have already been done. An iceberg once melted in the warm t h e Titanic was waters of the Atlantic ocean-nevertheless sunk.