INTERACTION BETWEEN NON-CONJUGATED CHROMOPHORES .9. EFFECTS OF HOMOCONJUGATED CYCLOPROPANE AND OXIRANE RINGS ON THE DIELS-ALDER REACTIVITY OF 2,3-BIS(METHYLIDENE)NORBORNANE

被引：23

作者：

PILET, O ^{[1
]}

CHOLLET, A ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,CH-1005 LAUSANNE,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 07期

关键词：

D O I：

10.1002/hlca.19790620731

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Preparation of 6exo, 7exo‐bis (methylidene)‐tricyclo[3.2.1.02,4]octane (6) is described. The reactivity of 6 towards tetracyanoethylene is evaluated and compared with that of exo‐2,3‐epoxy‐5,6‐bis (methylidene)norbornane (5), 2,3‐bis‐(methylidene)norbornane (1) and other related dienes. The cyclopropane group in 6 exerts an unsignificant rate retardation effect on the Diels‐Alder reactivity of this diene relative to that of 1, whereas a relatively important rate retardation effect is caused by the exo‐oxirane ring in 5. The observed effects are probably due to electronic factors (through‐space and through‐bond interactions). Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：2341 / 2349

页数：9

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