RACEMIZATION OF ALPHA-METHYL-ALPHA-ACETAMIDONITRILES

被引：10

作者：

FIRESTON.RA

REINHOLD, DF

GAINES, WA

CHEMERDA, JM

SLETZING.M

机构：

[1] Merck Sharp & Dohme Research Laboratories, Merck & Co., Inc, New Jersey 07065, Rahway

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 03期

关键词：

D O I：

10.1021/jo01267a060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of base-catalyzed racemization of α-acetamidonitriles bearing no enolizable α hydrogen has been studied and found to proceed via elimination and readdition of the elements of HCN; the amide nitrogen must bear a hydrogen atom. The rate-determining step is not deprotonation but expulsion of cyanide from the amide anion. © 1968, American Chemical Society. All rights reserved.

引用

页码：1213 / &

共 5 条

[1] MECHANISM OF DIMETHYL SULFOXIDE CATALYSIS IN NUCLEOPHILIC DISPLACEMENT
KINGSBURY, CA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (11) : 3262 - &
[2] THE EFFECTS OF SOLVATION ON THE PROPERTIES OF ANIONS IN DIPOLAR APROTIC SOLVENTS
PARKER, AJ
[J]. QUARTERLY REVIEWS, 1962, 16 (02): : 163 - 187
[3] SYNTHESIS OF L-ALPHA-METHYLDOPA FROM ASYMMETRIC INTERMEDIATES
REINHOLD, DF
FIRESTON.RA
GAINES, WA
CHEMERDA, JM
SLETZING.M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) : 1209 - &
[4] ACIDITIES OF WEAK ACIDS IN DIMETHYL SULFOXIDE
STEINER, EC
GILBERT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (19) : 3054 - &
[5] ALPHA-METHYLDOPA . RESOLUTION + CONFIGURATION
TRISTRAM, EW
TENBROEK.J
REINHOLD, DF
WILLIAMS, DE
SLETZINGER, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) : 2053 - &

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