Synthesis and Solvolytic Reactivity of endo-anti-and endo-syn-8-Tricyclo [3.2. 1.02, 4] octane Derivatives. Extensive Homoconjugative Participation by a Cyclopropane …

MA Battiste, CL Deyrup, RE Pincock…

Index: Battiste,M.A. et al. Journal of the American Chemical Society, 1967 , vol. 89, # 8 p. 1954 - 1955

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Citation Number: 40

Abstract

Dechlorination of V with sodium-THF-t-butyl alcoholg afforded the unsaturated ketal VII17 in 70 yield. The nmr spectrum of this compound showed relatively shielded olefinic protons at T 4.30, characteristic of the endo-tricyclo [3.2. 1. 02, 4] octene sy~ tem.~?'~ In addition, the spectrum did not reveal any unusual deshielding of a cyclopropyl methylene hydrogen by the bridge methoxyls which would be expected of an exo configuration. 11 Catalytic ...