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The Effects of Homoconjugated Cyclopropane and Oxirane Rings on the Diels-Alder Reactivity of 2,3-bis (methylidene)norbornane

✍ Scribed by Olivier Pilet; André Chollet; Pierre Vogel

Publisher: John Wiley and Sons
Year: 1979
Tongue: German
Weight: 566 KB
Volume: 62
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19790620731

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✦ Synopsis

Abstract

Preparation of 6__exo__, 7__exo__‐bis (methylidene)‐tricyclo[3.2.1.0^2,4^]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).

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