Photochemical cis-trans isomerization of 1,2-dibenzoyl-3-substituted cyclopropanes

被引：1

作者：

Chung, EH ^{[1
]}

Shim, J ^{[1
]}

Chae, WK ^{[1
]}

机构：

[1] Seoul Natl Univ, Dept Chem Educ, Seoul 151742, South Korea

来源：

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 1999年 / 129卷 / 1-2期

基金：

新加坡国家研究基金会;

关键词：

cis-trans isomerization; racemization; pi-pi interaction;

D O I：

10.1016/S1010-6030(99)00195-1

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Irradiation of cis, trans-1,2-dibenzoyl-3-methylcyclopropane (cis-1a) produced trans, trans-1,2-dibenzoyl-3-methylcyclopropane (trans1a). This cis-trans isomerization was shown to be reversible through cleavage of the bond beta to both carbonyl (1,2-bond fission) while irradiation of cis, trans-1,2-dibenzoyl-3-phenylcyclopropane (cis-1b) gave trans, trans-1,2-dibenzoyl-3-phenylcyclopropane (trans-1b) irreversibly through cleavage of the bond beta to both carbonyl groups (1,2-bond fission) and the bond beta to phenyl group (1,3-bond fission). 1,2-bond fission of optically active trans-1b showed racemization only under irradiation. This racemization of trans-1b was considered to be responsible for irreversible cis-trans isomerization of cis, trans-1,2-dibenzoyl-3-phenylcyclopropane (cis-1b). (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：43 / 48

页数：6

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