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- Title
Hyperconjugative Interactions in Bicyclo[2.2.1]heptane Derivatives. Effects on the Diels-Alder Reactivity of the s- cis-Butadiene Group of 2, 3-Dimethylidene-norbornanes.
- Authors
Hardy, Michèle; Carrupt, Pierre-Alain; Vogel, Pierre
- Abstract
Chemical and spectroscopic properties of the s- cis-butadiene chromophore in 2, 3-dimethylidene-norbornane can be modified without direct substitution of the diene moiety. Introduction of an etheral bridge for the H2C(7) bridge ( 2, 4, 6) and/or introduction of a double bond ( 5, 6) or of an exo-epoxide ring ( 3, 4) for the H2C(5)-H2C(6) bridge causes rate decreases in the Diels-Alder cycloaddition with dimethyl acetylenedicarboxylate. The differences of reactivity observed between the dienes 1- 6 are briefly discussed. Variation of the ability of the puckered cyclopentane ring of the bicyclo[2.2.1]heptane skeleton to hyperconjugate with the adjacent π-system is offered as a possible rationalization of the electronic effects.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 5, p1685
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590529