Additions and Corrections Vol. 34, 1969 Wendell L. Dilling, Charles E. Reineke, and Raymond A. Plepys : Pentacyclodecane Chemistry. V. The Synthesis and dec-6-yl Acetolysis of syn- and anti-Pentacyclo [5.3.0.0a,6.03,g.04,E] p-Toluenesulfonate. Evidence Concerning the Intermediacy of Bridges Carbonium Ions. Page 2605. Column 1. Under figures, “ O P C L ~should ’ read OPC14. Page 2607. Table 11, third column, second entry. “1.10 f 0.02 f should read 1.10 A 0.02 X low4. Page 2613. Column 2, line 26. “thered unction” should read the reduction. Page 2614. Column 1, equation. “kt” should read kt. Vol. 35, 1970 Wendell L. Dilling and Raymond A. Plepys : Metal Hydride (endoReductions of endo-Tricyclo[5.2. 1.0Z~e]deca-4,8-dien-3-one Dicyclopentadienone). Page 2972. Column 2, first equation. “LiAlHI” should read LiAlDa. Page 2975. Column 2, line 13. “ - 1.66” should read - 1.56. Denis M. Bailey and Robert E. Johnson : Reduction of Cyclic Anhydrides with XaBH4. Versatile Lactone Synthesis. Page 3575. Column 4, Table I. The method for glutaric anhydride should be B-2. Page 3575. Last line. In reference to the Vaughan, et al., w o k~ (ref 3) “camphoric anhydride” should read 2-methylnorbornane-endo-2,3-dicarboxylic anhydride and “a-campholide” should read camphenolide. Samuel P. McManus, John T. Carroll, and Charles U. Pittman, Jr. : Acid-Catalyzed Cyclization Reactions. IX. The Formation of Oxazolinium and Thiazolinium Cations from ?;-Allyl and Substituted Ar-Allylamides, -urethans, -ureas, and -thioureas. Page 3769. Scheme 11. In legend, “p-r, X = T” should read p-r, X = S. Structure 3 should appear as follows.
3 Vol. 36, 1971 C. A. Kingsbury* and R. A. Auerbach: Conformations of Certain Acyclic Sulfoxide Alcohols. Page 1739. A communication from 11. Nishio has led us to believe that our failure to observe nonequivalent hydrogens in the nmr spectrum of phenyl benzyl sulfoxide dissolved in trifluoroacetic acid was in error. Repetition of the experiment indeed did indicate nonequivalent hydrogens, as originally reported by Xishio. Page 1742. Compounds 10 and 11 were inverted. Compound 10 melts at 106”, and compound 11 melts at 129”. Peter Blumbergs,” Chandrakant B. Thanawalla, Arthur B. Ash, Claire N. Lieske, and George M. Steinberg: Synthesis and Stereochemistry of syn- and antz-p-Nitrophenyl Phenacyl Methylphosphonate Oxime. Page 2025. Column 2, line 37. The sentence starting with “Less reproducible . . . ” has a portion omitted and should read Less reproducible was the thermal isomerization of 2 to 1 by heating a deuteriochloroform solution of it at 50-55” for 40 min, and isomerization in deuteriochloroform at ambient temperature catalyzed b y DCl-D20. Tadashi Sasaki,” Shoji Eguchi, and Takeshi Toru : Synthesis of Adamantane Derivatives. XV. No Ring-Fission Aptitude of the Homoadamantan-4-one System in the Schmidt and Beckmann Rearrangements. Page 2455. Formulas 5 and 6 in Scheme I1 should be as follows.
5
6
Juane J. Silber and Henry J. Shine:* Ion Radicals. XXII. + C104-) with Reaction of Thianthrenium Perchlorate (C12HsS2. Aromatics. Page 2924. Column 2, Table 11. Heading for column 5 should read 10k,ppa. Page 2925. Column 1, Table IV. Heading for column 3 should read 10k’app,M-’ sec-l b . J. M. Babbitt,* H. Yagi, S. Shibuya, and J. T. Stock : Electrochemistry of Natural Products. 11. Electrolytic Oxidation of Some Simple 1,2,3,4-Tetrahydroisoquinoline Phenols. Page 3010. Column 2, line 43. “21” should read 20. J. F.,Wojcik* and I. J. Ostrich: Ionization Scheme for the N,N-Di( carboxymethy1)anilines. Page 3052. Table 11. Column 1 of data should read as follows. -1.3 f 0.2 -0.3 0.2 -0.4 f 0.2 0.2 0.2 0.5 0.2
+ + +
John C. Stowell : tert-Alkylnitroso Compounds. Synthesis and Dimerization Equilibria. Page 3055. We wish to call attention to a paper by J. E. Baldwin, A. K. Qvereshi, and B, Sklarz, J . Chem. SOC.C, 1073 (1969), in which the direct oxidation of 2,4,4-trimethyl-2-pentylamine to the nitroso compound is described. Jay K. Kochi* and C. L. Jenkins: 11. Kinetics of Ligand Transfer Oxidation of Alkyl Radicals. Evidence for Carbonium Ion Intermediates. Page 3103. The formula for allylcarbinyl chloride was incorrectly given as allyl chloride throughout the paper. B. D. Mookherjee,* R. W. Trenkle, and R. R. Patel: Synthesis of Racemic Muscone and Cyclopentadecanone (Exaltone) from lJ9-Cyclohexadecadiene. Page 3266. The name “Exaltone” used in this publication and in related publication on page 4124 is a trade-mark registered in the name of Firmenich & Cie, and should be spelled with a capital E. Harry Rubinstein,” James E. Skarbek, and Henry Feuer : Reactions of 3-Carboxyacryloylhydrazine and the Formation of Maleimides, Isomaleimides, and Pyridazinones. Page 3372. Formula 1 should be O H H O H HO--&-k=b-b-N-R Page 3372. Formula 4 should be O H H O H H HO-
tl-A
AcA-L
= - -
W. A. Mosher* and J, L. Brenner: The Synthesis of 2,4Diaryl-5H-indeno- and 2,4-Diaryl-5H-pyridocyclopenta[1,2-d]pyrimidin-&ones. Page 3383. The formula of compounds 7 should be as follows.
3753
t-” 1,
3754 J . Org. Chem., Vol. 37, N o . 23,1972 The formula of compounds 9a-e should be as follows.
Howard E. Smith* and Ann A. Hicks: Optically Active Amines. XII. Synthesis and Spectral Properties of Some Optically Active a-Oximino Ketones and a-Amino Ketone Hydrochlorides. Dimerization of a-Amino Ketones. Page 3667. Column 1, line 2. “0.507 g (5.07 mmol)” should read 0.155 g (0.507 mmol). B. D. Mookherjee,* R. R. Patel, and W. 0. Ledig: Synthesis of dl-Muscone from Exaltone (Cyclopentadecanone). Page 4124. The name “Exaltone” (a trademark) should be capitalized. Vol. 37, 1972
J. W. Huffman* and M. L. Mole: A Stereoselective Konannelation Synthesis of Eudalene Sesquiterpenes. Page 14. I n the structure for 10 and 11 R and R ‘ should be transposed. Graham F. Whitfield,* Rodney Johnson, and Daniel Swern: Clarification of the Acid-Catalyzed Reaction of Glyoxal with Carbamate Esters. Page 95. An important reference [P. R.1. Quan, J . Org. Chem., 33, 3937 (1968)l was overlooked in which the structure of the glyoxal-ethyl carbamate reaction product was clarified. Clayton H. Heathcock,” Rodney A. Badger, and Ronald H. Starkey: Photochemistry of lJ6-Cyclodecadienes. I. 1-Methyl- (E,E)-1,6-cyclodecadiene. Page 231. Name in title should be Ronald H. Starkey. George Just* and Phillip Rossy: The Action of Hydrazine and Its Derivatives on the Addition Products of Allyl Isothiocyanate and Dimethyl Malonate. A Correction. Page 318. Column 2. The structures for Va-d and VI11 should be given as follows. 0
Va, b, c, d,
X = Br X=I
VIII, x = I
X = OH X-ONO?
Thomas J. Barton,” Michael D. Martz, and Rodney G. Zika: Facile Bridge Expulsion of Sulfur Heterocycles. The 7-Thiabicyclo [2.2.1]hepta-2,5-diene and 7-Thiabicyclo [4.1.0]hepta-2,4diene Systems in Thiepin Synthesis. Page 554. Column 2. Insert the following at the end of the paper.
ADDITIONSAND CORRECTIONS Acknowledgment. -The authors are indebted to the Public Health Service (Grant No. GM 16689 from the Xational Institutes of Health) and the Petroleum Research Fund (PRF No. 1152-G1) for their generous support of this work. Zvi RapPoport* and Aharon Gal: Vinylic Cations from Solvolysis. X. SN1 and Nucleophilic Addition-Elimination Routes for 9-(a-Haloarylidene)Auoreness Page 1179. Table IV, column 3, lines 5 and 6. “13.5b and 0.29* ” should be 5 - 4 9 and 0.12b. Page 1181. Last line. Rreference 41 should be (41) R. C.Williams and J. M.Taylor, J. Chem. Educ., 47, 129 (1970). W. G. Dauben* and T. J. Dietsche: Stereospecific Introduction of Functionalized Angular Methyl Groups via the Claisen Reariangement. The Octalin and Hydrindenyl Ring Systems. Page 1216. Column 2. “Thermolysis of 13.” Line 6 and part of 7 should read (s, angular methyl a-methyl ketone) and 0.90 (s, angular methyl, P-methyl ketone). Philip E. Pfeffer,* Edward Kinsel, and Leonard S. Silbert: a-Anions of Carboxylic Acids. V. A Simple High Yield Presentation of a-Alkylhydracrylic Acids and a-8lkylacrylic Acids. Page 1256. In the second line of the title, “Presentation” should read Preparation. Albert W. Burgstahler, Donald E. Walker, Jr., John P. Kuebrich, and Richard L. Schowen:* A Convenient Synthesis of Benzaldehyde-formyl-d from Benzil. Page 1272. To the references cited in footnote 3 should be added the report of the versatile lithium aldimine route to 1-deuterio aldehydes by H. A I . Walborsky and G. E . Kiznik [ J . Amer. Chem. Soe., 91, 7778 (1969)] and A. F. Thomas’s monograph “Deuterium Labeling in Organic Chemistry,” Appleton-Century-Crofts, K’ew York, N. Y., 1971. R. C. Nickolson and Marcel Gut :* Stereospecific Synthesis of (20S,22R)-17a,20,22-Trihydroxycholesterol and (20S,22S)-17a,20,22-Trihydroxycholesterol. Pages 2119, 2120, 2122, 2125, and 2126. “sec-Butyllithium” should read isobutyllithium on page 2119, line 8, page 2120, Scheme 11, page 2122, column 1, lines 25 and 33, page 2125, column 2, line 62, and page 2126, column 1, lines 2 and 61. “seeButyl bromide’’ should read isobutyl bromide on page 2126, column 2, lines 64 and 70, and page 2126, column 1, line 6 . Delete footnote 27 on page 2125. R. A. Abramovitch,* S. R. Challand, and E. F. V. Scriven: Intermolecular Aromatic Substitution by Aryl Nitrenes. Page 2710. Insert the following at the end of the paper.
Acknowledgment.-The authors are grateful to the National Science Foundation (GP-18557) for the support of this work. Robert A. Ellison,* Warren D. Woessner, and Craig C. Williams: New Synthetic Methods from Dithianes. A Convenient Oxidation of Aldehydes to Acids and Esters. Page 2759. Column 2. In line 12 replace “methyl iodide” with n-butyl iodide. Gary N. Taylor: A Convenient Synthesis of Barrelene. Page 2904. I n column 1, paragraph 2, line 2, and Experimental Section, lines 3, 16, and 19, “I-” should read 2-.
