The relative rate of hydrolysis of a series of acyclic and six-membered cyclic acetals, ketals, orthoesters, and orthocarbonates

被引：82

作者：

Deslongchamps, P ^{[1
]}

Dory, YL ^{[1
]}

Li, SG ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Dept Chim, Synth Organ Lab, Sherbrooke, PQ J1H 5N4, Canada

来源：

TETRAHEDRON | 2000年 / 56卷 / 22期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ketals; orthoesters; orthocarbonates; stereoelectronic effects; hydrolysis;

D O I：

10.1016/S0040-4020(00)00270-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative rate of hydrolysis of these compounds is rationalized by considering the influence of steric, inductive and stereoelectronic effects on the hydrolysis reaction mechanism. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3533 / 3537

页数：5

共 35 条

[1] ALAZARD JP, 1977, B SOC CHIM FR II-CH, P499
[2] [Anonymous], CHEM HETEROCYCL COMP
[3] BUNTON CA, 1954, J ORG CHEM, V30, P1371
[4] MECHANISM AND CATALYSIS FOR HYDROLYSIS OF ACETALS, KETALS, AND ORTHO-ESTERS
CORDES, EH
BULL, HG
[J]. CHEMICAL REVIEWS, 1974, 74 (05) : 581 - 603
[5] HYDROLYSIS OF CYCLIC ORTHOESTERS - STEREOELECTRONIC CONTROL IN CLEAVAGE OF HEMIORTHOESTER TETRAHEDRAL INTERMEDIATES
DESLONGCHAMPS, P
CHENEVERT, R
TAILLEFER, RJ
MOREAU, C
SAUNDERS, JK
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (11): : 1601 - 1615
[6] Formation of cyclic ketals from hydroxyalkyl enol ethers, a stereoelectronically controlled endo-trig-cyclization process
Deslongchamps, P
Dory, YL
Li, SG
[J]. HELVETICA CHIMICA ACTA, 1996, 79 (01) : 41 - 50
[7] Deslongchamps P., 1983, ORGANIC CHEM SERIES, V1
[8] DEWOLFE RH, 1970, CARBOXYLIC ORTHO ACI, P134
[9] EIKEREN PV, 1980, J ORG CHEM, V45, P4641
[10] CONFORMATIONAL ANALYSIS .17. 2-ALKOXY- AND 2-ALKYLTHIOTETRAHYDROPYRANS AND 2-ALKOXY-1,3-DIOXANES . ANOMERIC EFFECT
ELIEL, EL
GIZA, CA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10) : 3754 - &

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