THE MECHANISM OF ACYLCARBENE INSERTION INTO O-H BONDS - DIRECT OBSERVATION OF THE ENOL OF A CARBOXYLIC-ACID ESTER IN AQUEOUS-SOLUTION

被引：28

作者：

CHIANG, Y

KRESGE, AJ

PRUSZYNSKI, P

SCHEPP, NP

WIRZ, J

机构：

[1] UNIV TORONTO,DEPT CHEM,TORONTO M5S 1A1,ONTARIO,CANADA

[2] UNIV BASEL,INST PHYS CHEM,CH-4056 BASEL,SWITZERLAND

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 10期

关键词：

D O I：

10.1002/anie.199113661

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The addition of water to the acyl carbene function as a whole is a better description for the reaction (a) than the insertion of carbene 1 into the O-H bond of water. The enol tautomer 2 of methyl mandelate was shown to be an intermediate. If the photolysis is conducted in O-18-enriched water, 3 is marked exclusively at the alpha-hydroxyl group.

引用

页码：1366 / 1368

页数：3

共 18 条

[1] Bell R.P., 1966, ADV PHYS ORG CHEM, P1, DOI [10.1016/S0065-3160(08)60351-2, DOI 10.1016/S0065-3160(08)60351-2]
[2] THE ENOL OF MANDELIC-ACID, DETECTION, ACIDITY IN AQUEOUS-SOLUTION, AND ESTIMATION OF THE KETO-ENOL EQUILIBRIUM-CONSTANT AND CARBON ACIDITY OF MANDELIC-ACID
CHIANG, Y
KRESGE, AJ
PRUSZYNSKI, P
SCHEPP, NP
WIRZ, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07): : 792 - 794
[3] CHIANG Y, 1989, Z NATURFORSCH A, V44, P406
[4] CHIANG Y, 1990, ANGEW CHEM, V102, P810
[5] CIGANEK E, 1970, J ORG CHEM, V35, P862
[6] FUJIWARA Y, 1987, J AM CHEM SOC, V10, P1942
[7] MECHANISMS OF GENERAL ACID AND BASE CATALYSIS OF REACTIONS OF WATER AND ALCOHOLS WITH FORMALDEHYDE
FUNDERBURK, LH
ALDWIN, L
JENCKS, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) : 5444 - 5459
[8] GILCHRIST TL, 1969, CARBENES NITRENES, P72
[9] ACIDITY OF ACETOPHENONE ENOL IN AQUEOUS-SOLUTION
HASPRA, P
SUTTER, A
WIRZ, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08): : 617 - 619
[10] HASPRA P, 1979, ANGEW CHEM, V91, P652

← 1 2 →