AN INDEX TO THE LITERATURE OF
STEREOCHEMISTRY, WITH A NOTE ON THE STEREOCHEMISTRY OF CREATIKINES.
BY DR. ARNOLDEILOART.
I n compiling this index I have been much indebted to t h e numerous references in Van’t Hoff-Meyerhoffer’s ‘‘Stereochemie,” most of which, with amplifications and some corrections, are incorporated here ; also to the bibliography, by Prof. Wardor, of which I have made free use. To Dr. Henry Carrington Bolton my thanks are due for valuable advice as well as for bibliographical data; in particular for calling my attention to Swedenborg’s contribution to stereochemistry. PLAN OF INDEX.
T h e bibliography of this subject published two years ago by Warder having been classified according to subjects, I have arranged the present list in the order of the authors’ names, hoping that thus the maximum benefit may accrue from the existence of both indexes, which may be used together. But in order that this index may be capable of independent w e as a guide to the litertiture of any given branch of the subject a symbol is prefixed to each paper, excepting only those of scope too wide to admit of such brief indication of their subject matter. A list of symbols precedes the list of papers. For clearness, only the main subject of each paper has been in-
242
LITERATURE O F STEREOCHEMISTRY.
dicated by a symbol; thus a paper marked
9 d may treat
not
only of ring-configurations but of rings containing an asymmetric carbon-atom (C) ; yet if ring-configuration is the main subject, the symbol C will not appear. Whether or not a paper on optical activity bears mainly on the question of the asymmetric carbon-atom is often difficult to decide. For most cases I have settled the question by marking with C only papers which were printed after those of Van’t Hoff and Le Bel in 1874. I n doing this I have simply accepted as a separate epoch the period which these chemists made such by their work. Earlier papers on the action of substances on polarized light are marked L for ‘(Light.” As the great bulk of stereochemical investigation has been massed together in point of time, a chronological index seemed useless; on the other hand many a reader may wish to consult the literature of a particular period or to see at a glance the general chronological distribution of the literature; the few lines necessary t o satisfy such readers have therefore been added in the form of a classification of publications into periods. Finally, since a specially helpful form of guidance consists in information as to other guides, and since so many must make compactness and not originality the criterion of what they shall read, a list of reviews of the main subject and of its chief branches is given.
L I S T O F SYMBOLS AND CONTRACTIONS. C = stereochemistry of carbon.
C = asymmetric carbon. I for I = ethane derivativee. 0 C I I for I1 = ethylene derivatives. C
LITERATURE OF STEREOCHEMISTRY.
V for
0
L
--
243
= “Cis-trans” isomers.
= Benzene and derived rings. Action on polarized light.
N = Nitrogen except pentavalent nitrogen.
NV = Pentavalent nitrogen.
Ann. = Ann. Chem. (Liebig.) Ber. = Ber. d. Chem. Ges.
R. = My review of Stereochemistry.‘ The figures following R indicate the page or pages of the review on which the reference or references preceding R, and placed in parenthesis with it, are given. This affords a ready means of gaining some idea of t h e contents of the papers so bracketed. ‘About to appear independently with this index as an appendix.
LIST OF PUBLICATIOKS.’
1.
I
2.
c II
I C
II
c
3. 4.
A I
I
v II A
I
1
v ‘./
Alexander, H.--1888. Ann. 248, 281. Phenylmalic acids. Anschutz, R.-1887. Ber. 18, 1949. The number of inactive malic acids. 1887. Am. Chem. J. 9, 2 5 3 ; Chem. Ztg. 11, 1212 ; Ann. 239, 161.-1889. (Ann. 254, 168.-R. 20).* Fumaric and maleic acids.--1890. (Ann, 259, 145-E. 32). “ and Bendix, P.-1890 Ann. 259,62. Diphonylsuccinnic acids. Relationship probably same as between the hydrobenxoins. ‘‘ and Hintze, C.-l885, Ber. 18, 1394. Attempt to “double” oxalic acid. 1887. Ann. 239, 164. Attempt to ”double” fumaric acid. ‘( and Selden, Ch. C.-lSS’i Am. Ghern. J. 9, 379 ; Ber. ’LO, 1382. Monobromcinnamic acids. Antrick, 0.-1887. Ber. 20, 310. Cocaine. Armstrong, H. E.-1887 (J. Chem. SOC. 51, 264.-R. 14). 2588. Ibid. Proc. 54, 93 (Ref. Chem. News 58,240). Plane and axial symmetry. 1892. Chem. News 65, 285. New structural f o r m u l ~suggested for acids supposed to be sterecmeric.2
In several instances the references to the Berichte given in this index differ from those in the Berichte indexes, which contain numerous errors ; some of them really recherches. e This word, introduced by Van’t Hoff-Meyerhoffer, is used instead of the awkward “ stereo-isomeric.”
LITERATURE OF STEREOCHENISTRY.
2445
Aronstein, L., and Hollemann, A. F.-1889 Ber. 22, 481. Addition of H to acetylene compounds. Chem. News 60, 235. Forms of 6. - Ashe, Isaac.--1889. Atoms. 7 . - Aubin, Ch. See Graebe, C. Ber. 20, 1531. Thiophenylcro5. II Autenrieth, W.-lSW. tonic acids. (E. Baumann’s laboratory.) Auwers, K.-1890. Die Entwicklung der Stereo9. chemie. Theoretische und experimentelle Studien.” Heidelberg : C.Winter, pp. 157. 1890. Ber. 23, 299. N 1891. Ber. 24, 1776. Hydrobenzofns. I lS90 and ’91. Uer. 23, 1600; 24, 4012. Dimethylglutaric acids. 66 and Dittrich, Bf.-lSS9. Ber. 22, 1996. x Structure of benziloximes. (6 and Jackson, Louis L.-1890. Ber. 23, I 1509. Bisclioff’s dynamic isomerism. 66 and Kiibner, E.-lY91. Ber. 24, 1923. I Symm. dimethylglutaric acids, etc. (6 and Neyer, V.-lSSS. Ber. 21, 7S4, 3510. N Two benzildioxinies. 1889. Ber. 22, 537. Two benzilmonoximes. Ber. 22, 564. Structural identity of benzilmonoximes.-Ber. 22, 705. The third benzi1dioxime.-Ber. 22, 1989. KO isomeric oximes of phenanthraquinone. Ber. 22, 2011. T’etramethylsuccinic acids. I Ber. 22, 3005. Dibasic acids, C,H,,O,. Katnrmiss. Rundschau 4, 477-481. Present state of stereo-chemical investigation. (Ref. Chem. Centrbl. [4] 1, II., 668. 1S90. Ber. 23, 101. Formation of anhyI drides of acids of succinic series. Facilitated by presence of alkyls. 5.
II
((
246
LITERATURE OF STEREOCHEMISTRY.
N Auwers, K., and Jleyer, 17.-(J3er.
I N
N
-
10. 11. I I 12.
”*J
-
23, 2063.-R. 43.) Oximes of halogenised benzophenones.(Ber. 23, 2403.-R. 44.) Configuration of hydroxylamine. (Bey. 23, 2079.-R. 2 5 , ) Ethane derivatives. 1891. (Ber. 24, 3267.-Ii. 4’7.) Oximes, ,411swcr to C l a w Ber. 24, 4225.--R. 44. Isomeric hydrazones. lr and Siegfeld, M.-l892. Ber. 25, 2597. Benziloximes. Testing structural identity. Auwers, K. See Fehrlin, 11. C. CC Krause, A. I( ii Meyer, V. Bachmeyer, W.-l886. Clhem. Centrbl. [3] 16, 209. Molecular spheres and molecular structure. Bader, R.-1890. Ztschr. phys. Chem., 6, 289 (espec. p. 315). Affinity constants. Baeyer, A. von.-1870. Ann. Supp. 7, 1. Mellithic acid. 3885. Ber. 18, 674, (8269.-R. 10). Polyacetylene compounds. (See especially p. 2278.) 1886-’91. Ber. 19, 1797; (23, 1272.-R. 10). Ann. 245, 103 ; 2 5 1 , 2 5 7 ; 256, 1 ; 258, 1, 145; 266,169. Constitution of benzene.’ (R. 14, 26.) 1888. Ann. 246, 383. Note on L. Meyer’s Benzene forniula. 1898. Ann. 269,145. Constitution of benzene. Baker, H. B.-l888. Chem. Kews, 48, 187. Nitrogen and hydrogen said not to combine in presence of spongy platinum. (But see Johnson, G. s.) Bamberger, E.-l890. (Ann. 2 5 1 , l ; J. prakt. Chem. [2] 42, 188.-R. 14, 15.) Ber. 23, 291. “Doubling“ of ac. 1, 5 , tetrahydronaphthalene diamine. Bandrowski, E.-1879. (Ber. 12, 2212.-R. 18.) ((
0I I
c 13. N
14.
v C 15. II
lA special connection between para4oms (Clam’ formula), said to exist side by side with the general central connection among all six atoms.
LITERATURE OF STEREOCHfiMISTRY.
247
16. - Barbieri, J. See Schulze, E. 17. C Baumann, E.-l882. Ber. 15, 1731. Cystine derivatives. Activity and C disappear together. '6 See also Autenrieth, W. .../ - and Fromm, E.-1891. (Ber. 24,1419.-R.15). 18. N Beckmann, E.-l887-'90. (Ber. 20,2766 j 22, 429, 514, 1531, 1588 ; 23, 1680, 3319, 3331.-R. 43.) Benznldoximes. '-./ 1889. Ann. 250, 322. Camphor series. (Theory, pp. 360-375.) C' See Giinther, E. (' dee Pleissner, M. 19. - Beckurts, H.-See Otto, R. 20. N Behrend, R.-l890. (Bel-. 23, 454, 1776-R. 38, 45.) N-poles. " and K6nig, E.-l890. Ber. 23, 2750. TWO isomeric paranitrobenzylbenzaldoximes. '' and Leuchs, K.-1889-'90. Bcr. 22, 384, 613; Ann. 258, 44; 257, 202. Hydroxylamine derivatives. I' and Nissen, Det1ev.--2892. Ann. 269, 390. 0-chlorbenzaldoximes. 21. C Beilstein, F., and Wiegand, E.-1883. Ber. 17, 2261. Tiglic :uid angelic acids. 22. - Bendix, P. See Anschiitz, R. 23. C Berthelot, D.-1875. (Bull. SOC. cliim. (Paris) [2], 23, 338.-R. 49.)-1876 and 1878. Comptes rend. 82, 441, 85, 1181. Styrolene said to be opticaljy active, Compare Hoff, J. H. van't, also Krakau. 24. - Besredka, A, See Zelinsky, N. 25. I Bethmann, H. G.-189i). (Ztschr. phys. Chem. 5, 385-R. 25, 28.) 26. L Biot, J. B.-1817. MQm. de 1'AcadLmie de Paris' 2 41 (especially pp. 114 et seq.). Turpentine vapor optically active.
0
The date is a better guide than the volume, a8 the series seem to be confused.
24s
LITRRATUHE OF STEREOCHEJlISTRY
L
Biot, .i13.-lSlS. .
Ibid 1 3 , 144(?).’ Ann. cliirn. p l i ~ ~ .
E?] 9,
372. Ann. chini. phys., 1 0 , 63. Optical activity of w r i o u s snbstaiices. ld33. Ibid. 13, 39. Applications to oivganic chemistry. 18:‘s. Ibid. 13, 93. Optical activity of mixtures and con1bin:itions. JY38. Ibjd. 69, 2 2 . Polarized light sliows ilifYereiicc Iwtn.ecn isomers. l.S3!\. C’omptcs rend., 9, 621. Activity of T 11 rpen t i n e. cii m ph o r .-1b i d. 9, S2 5. ( C 0 11113. J k v i 111:. ) 1S4-i. Ann. c l i i r n . pilps. [SI 10, j 17.5, 307, 3 8 5 : 11, S?. [Tee of polarized light, f o r s t u d j i n g cliemical nieclianice. 1S48-‘20. Clomptes rend., ’2’7, 4G1: 29, 433; 3 1 , G01. IZc>poits011 1’astc:iir’s work 011 the tiirtaric ;Lcids.-Ibid. 28, 3.21 : Camphoiic acid (comp. 12oucliardatj.-Ibid. 29, GS1 : A 1 ~ i ncliim. . plijs. [S] 28, 215: 351. Rotatioii 1 3 ~soiids.--Comptea rend., 30, 7?1 : .\nii. rliim. phys., 29, 133, 341. Tartaric i i c icl s. C‘oniptes rend. 31, 101. Ann. cliirn. pliys., 29, 430. Laws of variation of rotatory 1’0”’”’’. 1Sj.l. Compte3 rend. 33, 549. Report on Pmteur’s paper i n Xiin. chim. pliys. [3] 34, 30. Bischoff, C. A.-lSSG-’S7. Her. 19, 93: 20, 295s. Substituted succiiiic iiciils. 1858. ISer. 21, 2071 (especially p. 2074). ~itrostilbeiies.-Ber. 21, 2102. Symm. diethylsuccinic acids : especially pp. 5105 1519.
27,
I
et seq. See note on last page.
LITERATURE O F STEREOCHEMISTRY.
N Bischoff, C. A.-l889.
I II
N
N
rr
I
rr
I I
I
i C
rr
rr
N
I
rr
N
rr
I
66
I
rr
249
Ber. 22,1774,1792,1809. Piperazines and derivatives. 1889-’90. Ber. 22, 3179; 23, 13. Substituted succinic acids. 1890. (Ber. 23, 1924--.R. 21.1 (Ber, 23, 1967-R. 47.) Ber. 23, 1972. Piperazine group. (Ber. 23, G20, G23, 1464, 3414; 24, 1041, 1050, 1064, 10‘74, 1085, 2001.-R. 26, 3034.) Dynamic isomerism. 1891. Ber. 24, 2083. Substituted succinic acids. and Huusdorfer, A.-l890. Ber. 23, 1981, 1987, 1991, 1997, 2003. Piperazine derivatives. and Hjelt, E.-lY87 and 1888. Ber. 20,2988, 3078; 21, 2089, 2097, 2102; 22, 6 7 ; 23, 650. Substituted succinic acids. Ber. 23, 634, and Kuhlberg, A. von.-ld90. 1042. Substituted succinic acids. and Mintz, N.-1890. Bel*. 23, 647, 653, 65G, 3410. Substituted succinic acids. and Nastvogel, 0.--1889. Ber. 22,1783,1786, 1804. 1890. Ber. 23, 2026, 2031, 2035, 2040, 2047, 2051. Piperazine derivatiyes.-Ber. 23, 2055, Attempts to prepare rings containing two nitrogen and two, three or six carbon atoms. and Rach, 0.-1885-’86. Ber. 18, 1202; Ann. 234, 54 (especially p. 86). Symm. dimethylsuccinic acid. and Trapesonzjanz, Ch.-l890. Ber. 23, 197‘7. Diphenylpiperazine. and Voit, E.-1889-’90. Ber. 22, 389; 23, 630, 644. Symm. dimethylsuccinic acids. and Walden, P.-l889. Ber. 22, 1812, 1819. Disubstituted succinic acids.
2 50
LITERATURE OF STEREOCHEMISTRY.
I 28. I 1
29. II 30. C 31.
-
32. 33. L
C 34. N 35. -
36. 37. 38. C
-
C
Bischoff, C. A . , and Walden, P.-1890. (Ber. 23, 1950. -R. 7 . ) Blank, A.-1888. (Ann. 248,l.--H. 24.) Members of the stilbene group. (Communicated by Wislicenus, J , ) Compare Eiloart, h., and Redzko, IF-. G. Bleibtreu, €1.-1546. Ann. 59, 153. Cumaric acid. Bornstein, E., aud Herzfeld, A1.-1885. Rer. 18, 3353. Trioxybutyric acid. Boltzmann, L.-I 589. Terein deutsch. Naturforscher, Sept. 21. (Ref. Chem. Centrbl. [4) 1, 11, 67’7.) Relation between size of molecule and space occupied by the valences. Bosshard, E. See Xchulze, E. Bouchardat, G.--1843. Ann. chim. phya. [SI 9, 213. Optical activity OP alkaloids. 1844-’45. Comptes rend. 18, 295 ; 20, 1635. Optical activity of salicine, etc.-Ibid. 19, 601, 1174. bmygdaline and amygdalic acid. 1849. Comptes rend. 28, 319. Camphoric acid. Comp. Biot. 1672. Ibid 74, 665. Dulcite derivatives. (‘ and Lafont.-188’7. Comptes rend. 105, 1177. Borneols. Braun, E.-l859. Ber. 22, 5 5 7 . Benzilmonoxime. Brown, F. D.-lSSl. Chem. S e a s , 44, 195. Affinity and valence. Browne, G. hl. See Michael, A. Bredig, G. See Will, W. Bremer, G. J. V7’.--1880. Ber. 13, 351. Recueil trav. Chim. 4, 180. “Doubling” of malic acid. 1885. Ibid. 6, 255, Effect of different solvents on specific rotation. and Hoff, J. H. van’t-1876. Ber. 9, 215. Optical activity disappears with C. ((
LITERATURE OF STBREOCHESIISTRY.
39, I t
40. I1 I*,
w
41.. ).J 42. 43. NT 44. 45.
-
-
46. I 47. L
48. L
49. I1
c
50.
-
51.
-
251
Bruck, P.-l891. Ber. 24, 4118. Addition of iodine t o ansaturated acids. 1892. Ber. 25, 503. Correction of above. Briihl, J. W.-1881. Bey. 14, 2742. Citraconic and niesaconic acids. 1887. Ztwhr. phys. Chem. 1, 307; Ber. 20, 2288. Refractive power and oonstitution of benzene and naphthalene compounds. 1892. Ber. 25, 1052. Trimethylene. Straintheory. Buchner, E., and Dessaiier, H.-l892. Ber. 25, 1147. Carboxyl derivatives of phenyltrimethylene. Buchstab, L. See Zclinsky, N. (J. Chem. Soc., Burcli, G. J. and MarRh, J. E.-1889. 65, 65G.-R. 40.) Caberti, L. See Minunni, G. Carnelley, T.-1882. Phil. Mag. [5], 13, 112, 180. Influence of atomic arrangement on the physical properties of substances. Chalanay, L., and Knoevenagel, E.-1892. Ber. 25, 289. Stereomeric diphenylsuccinic nitriles. Chancel, G.-1869. Comptes rpnd. 68, 659, 726. Propyl alcohol said to be active; but see Henninger, A. Chautard, J.-Jsb. Chem. 1863, 556. The two camphoric acids. Ciamician, G.-1888. Ber. 21, 1621. Apiol and isapiol. '( and Magnanini, 6.-1886. Gazz. ~ h i r n . 1 6 ~ 3 9 0 . Two tetrabromides of piperylene. 1888. Ber. 21, 1434. omeric I I > ~ ! ~ ~ z o I~i ~ P iS ~ - l l i t ~ ~ ~ l i ~i l c~l d~s .~
s 51. C
( L s b o r a t o q of Auwers id l l c j e r . ) Fischer, E.-l8P4. 'S< arid 'hi). Rer. 1 7 , 279 : 21, 988, P G , i 1 ; 2'2, 87. l'lienplhydrazinc compounds For w l t l l sug,il's, l'ts. 1, 111. IV R l i t l Y. l't. 11, w e Flsclier aiid Steclie. A. i b p ' ~ . 1( ' i ( 111 tletitsrh. Saturforscher, Sept. 19th c l l l t l ? 2 d . (Ref. C'heni. C'eiitrbl. [J]
1, 11, G 2 . j 18Q0. E e l , 2:j, 3 ;O. Syntliesre. Xaiiiionlc w ~ d tlonhled" (p. 379).--1b. 7'99. S p the& of grape augar.--Ibid 9114. Lecture on syntheses in t h e sugar group. with bibliograpli~.--lbicl 2611. Optical isomers of g!ucosc~.ctc.-Ibid 9625. Acids of the sugar g i oup.--I'uiJ 3iis4. Ileductioii of fruit sugar. 1h01. Rei. 34, 1836. 9683. Configuration of gl~iL05e:tilt1 i t a isomc'rs (Ref. A m . C'hem. J., 14, 309). -Her. 24, 2136, 3622. S e w isomer of miicic acid. 1 ~ 9 2 . A\nn. 270, 64. Sugars from glucose with more tlian six carbon-atoms. and Ciirtibs, I:. S.-1892. Ber. 25, 1025. (T ulon 1 r tic i (1-. and Hertz. ,J.--lS92. Rer. 23, 124;. Mucic acid. and -IIirbdliberger, .J.-lSSS aiid '89. Her. 21, 1805 ; 23, 365, 1165, 3213. Mannose. and Meyer, .J.-1889. Ber. 22, 361, 1941. Oxidation of milk-sugar and of maltose. and Passmorc, F.-1889. Ber. 88, 359. 1890. Ber. 23, 2226. Sugar. +
C
90. Ber. 23, 1;s;. Isomerism of certain nitrogen coniporiiids. 'r and IZitsclike. -1-1S90. 13er. 25. 1;3>. Gaudin, ?ilarc-A1itoine.-IS;5. '( li'hrcllitecture d u llonde des Atomea." Paris, IS;3. Gautliier-\7illars, pp. xix+i?31. Compare Klrst. Gernez, D.-l864. Ann. scient. de 1'Ecole normale sup. 1 , 1. Optical activity of turpentine and camphor vapors. Giesel, F. See Liebermann, C. Goldschmidt, H.-lS89 and'90. (Ber. 22, 3101 ; 93,2163, 9746.--R. 13.) 23, 3113. Benzaldoxinies are strncturally identical. and Ernst, H. T.--1890. Ber. 23, 2170. 0sini es. and Kisser.-l887. Ber. 30, '5071. Carvoximes. " and Kjellin, C.-l891. Ber. 2.1, 2547. P-nitrobenxaldoximes. Goldschmiedt, G.-lS&5, Sitz. Ber. Akad. TVien, January : Monatsh. Chem., 9, 42. (Ref. Ber. 240. Papaverine. ) Graebe, C.-l887. Ber. 20, 548. Diphenic acids. Formuh. 1S90. (Rer. 23, 1344.--H. 26.) Benzilorthocarboxylic acid (especially p. 1347).
