Synthesis and reactivity of exo-and endo-bicyclo [2.1. 0] pentan-5-ol and their derivatives

JJ Tufariello, AC Bayer…

Index: Tufariello,J.J. et al. Journal of the American Chemical Society, 1979 , vol. 101, # 12 p. 3309 - 3315

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Citation Number: 7

Abstract

Abstract: A rational synthesis of 5-substituted bicyclo [2.1. O] pentanes was developed from the Diels-Alder adduct of 6, 6-dimethylfulvene and dimethyl azodicarboxylate. Kinetic investigations indicate enormous reactivity for derivatives of endo-bicycl0 [2.1. O] pentan-5- ol, and a mechanism for solvolysis of the exo-p-nitrobenzoate, which proceeds via the corresponding endo isomer, is outlined

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