Clarification of the Acid-Catalyzed Reaction of Glyoxal with Carbamate

Clarification of the Acid-Catalyzed Reaction of Glyoxal with Carbamate Esters. Graham F. Whitfield, Rodney. Johnson, and Daniel. Swern. J. Org. Chem. ...
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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-.