1ST EXPERIMENTAL-EVIDENCE FOR A SYNPERIPLANAR STEREOELECTRONIC EFFECT IN THE ACID-HYDROLYSIS OF ACETAL

被引：38

作者：

LI, SG

KIRBY, AJ

DESLONGCHAMPS, P

机构：

[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA

[2] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(00)61558-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tricyclic acetal 1 in which the ring oxygen has an electron pair synperiplanar to the C-OMe bond can be readily hydrolyzed with HCl 0.1N

引用

页码：7757 / 7758

页数：2

共 17 条

[1] COMPLETE KINETIC ISOTOPE EFFECT DESCRIPTION OF TRANSITION-STATES FOR ACID-CATALYZED HYDROLYZES OF METHYL ALPHA-GLUCOPYRANOSIDES AND BETA-GLUCOPYRANOSIDES [J].

BENNET, AJ ;

SINNOTT, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7287-7294

[2] IMPORTANCE OF CONFORMATION OF TETRAHEDRAL INTERMEDIATE IN HYDROLYSIS OF ESTERS - SELECTIVE CLEAVAGE OF TETRAHEDRAL INTERMEDIATE CONTROLLED BY ORBITAL ORIENTATION [J].

DESLONGC.P ;

FREHEL, D ;

ATLANI, P ;

MALAVAL, A .

CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (20) :3405-&

[3] INTRAMOLECULAR STRATEGIES AND STEREOELECTRONIC EFFECTS - GLYCOSIDES HYDROLYSIS REVISITED [J].

DESLONGCHAMPS, P .

PURE AND APPLIED CHEMISTRY, 1993, 65 (06) :1161-1178

[4]

DESLONGCHAMPS P, 1983, ORGANIC CHEM SERIES, V1, P41

[5]

DESLONGCHAMPS P, IN PRESS INTRAMOLECU

[6] THE ANOMERIC AND REVERSE ANOMERIC EFFECT - A SIMPLE ENERGY DECOMPOSITION MODEL FOR ACETALS AND PROTONATED ACETALS [J].

GREIN, F ;

DESLONGCHAMPS, P .

CANADIAN JOURNAL OF CHEMISTRY, 1992, 70 (05) :1562-1572

[7] ON THE NATURE OF THE ANOMERIC EFFECT IN XHN-CH2-OH SYSTEMS, WITH X = F, O, N, C [J].

GREIN, F ;

DESLONGCHAMPS, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (02) :604-611

[8]

GREIN F, 1993, IN PRESS ACS MONOGRA

[9] STEREOELECTRONIC ASPECTS OF THE ANOMERIC EFFECT IN FLUOROMETHYLAMINE [J].

IRWIN, JJ ;

HA, TK ;

DUNITZ, JD .

HELVETICA CHIMICA ACTA, 1990, 73 (07) :1805-1817

[10]

Kirby A. J., 1983, REACTIVITY STRUCTURE, V15

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