Correction. Stereospecific Synthesis of (20S,22R)-17α,20,22-Trihydroxycholesterol and...

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3754 J. Org. Chem., Vol. 37, No. 23, 1972 ADDITIONS AND CORRECTIONS 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. “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. Column 1, line 2. Vol. 37, 1972 J. W. Huffman* and M. L. Mole: A Stereoselective Kon- annelation Synthesis of Eudalene Sesquiterpenes. Page 14. In 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. 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-Meth- yl- (E,E)-1,6-cyclodecadiene. Page 95. Page 231. George Just* and Phillip Rossy: The Action of Hydrazine and Its Derivatives on the Addition Products of Allyl Isothio- cyanate and Dimethyl Malonate. Page 318. Column 2. The structures for Va-d and VI11 should be given as follows. Name in title should be Ronald H. Starkey. A Correction. 0 Va, X = Br b, X=I c, X = OH d, X-ONO? VIII, x = I Thomas J. Barton,” Michael D. Martz, and Rodney G. Zika: Facile Bridge Expulsion of Sulfur Heterocycles. The 7-Thia- bicyclo [2.2.1] hepta-2,5-diene and 7-Thiabicyclo [4.1.0] hepta-2,4- diene Systems in Thiepin Synthesis. Insert the following at the end of the paper. Page 554. Column 2. 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 “13.5b and 0.29* should be 5-49 and 0.12b. Page 1179. Table IV, column 3, lines 5 and 6. 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 Intro- duction of Functionalized Angular Methyl Groups via the Claisen Reariangement. 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. To the references cited in footnote 3 should be added the report of the versatile lithium aldimine route to 1-deuterio aldehydes by H. AI. 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. “sec-Butyllithium” should read isobutyllithium on page 2119, line 8, page 2120, Scheme 11, page 2122, column 1, lines 25 and 33, page 2125, col- umn 2, line 62, and page 2126, column 1, lines 2 and 61. “see- Butyl bromide’’ should read isobutyl bromide on page 2126, col- umn 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. Acknowledgment.-The authors are grateful to the National Science Foundation (GP-18557) for the sup- port of this work. Robert A. Ellison,* Warren D. Woessner, and Craig C. Wil- liams: New Synthetic Methods from Dithianes. A Con- venient Oxidation of Aldehydes to Acids and Esters. Page 2759. Column 2. In line 12 replace “methyl iodide” with n-butyl iodide. Gary N. Taylor: Page 2904. The Octalin and Hydrindenyl Ring Systems. Page 1272. Pages 2119, 2120, 2122, 2125, and 2126. Insert the following at the end of the paper. A Convenient Synthesis of Barrelene. In column 1, paragraph 2, line 2, and Experi- mental Section, lines 3, 16, and 19, “I-” should read 2-.

Transcript of Correction. Stereospecific Synthesis of (20S,22R)-17α,20,22-Trihydroxycholesterol and...

3754 J . Org. Chem., Vol. 37, N o . 23, 1972 ADDITIONS AND CORRECTIONS

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. “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.

Column 1, line 2.

Vol. 37, 1972

J. W. Huffman* and M. L. Mole: A Stereoselective Kon- annelation 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.

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-Meth- yl- (E,E)-1,6-cyclodecadiene.

Page 95.

Page 231. George Just* and Phillip Rossy: The Action of Hydrazine

and Its Derivatives on the Addition Products of Allyl Isothio- cyanate and Dimethyl Malonate.

Page 318. Column 2. The structures for Va-d and VI11 should be given as follows.

Name in title should be Ronald H. Starkey.

A Correction.

0

Va, X = Br b, X = I c, X = OH d, X-ONO?

VIII, x = I

Thomas J. Barton,” Michael D. Martz, and Rodney G. Zika: Facile Bridge Expulsion of Sulfur Heterocycles. The 7-Thia- bicyclo [2.2.1] hepta-2,5-diene and 7-Thiabicyclo [4.1.0] hepta-2,4- diene Systems in Thiepin Synthesis.

Insert the following at the end of the paper.

Page 554. Column 2.

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

“13.5b and 0.29* ” should be 5-49 and 0.12b.

Page 1179. Table IV, column 3, lines 5 and 6.

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 Intro-

duction of Functionalized Angular Methyl Groups via the Claisen Reariangement.

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.

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.

“sec-Butyllithium” should read isobutyllithium on page 2119, line 8, page 2120, Scheme 11, page 2122, column 1, lines 25 and 33, page 2125, col- umn 2, line 62, and page 2126, column 1, lines 2 and 61. “see- Butyl bromide’’ should read isobutyl bromide on page 2126, col- umn 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.

Acknowledgment.-The authors are grateful to the National Science Foundation (GP-18557) for the sup- port of this work.

Robert A. Ellison,* Warren D. Woessner, and Craig C. Wil- liams: New Synthetic Methods from Dithianes. A Con- venient Oxidation of Aldehydes to Acids and Esters.

Page 2759. Column 2. In line 12 replace “methyl iodide” with n-butyl iodide.

Gary N. Taylor: Page 2904.

The Octalin and Hydrindenyl Ring Systems.

Page 1272.

Pages 2119, 2120, 2122, 2125, and 2126.

Insert the following at the end of the paper.

A Convenient Synthesis of Barrelene. I n column 1, paragraph 2, line 2, and Experi-

mental Section, lines 3, 16, and 19, “I-” should read 2-.