The Journal of Organic Chemistry

The protonated cyclopropane route to bicyclic cations

W Kirmse, J Streu

Index: Kirmse, Wolfgang; Streu, Joachim Journal of Organic Chemistry, 1987 , vol. 52, # 4 p. 515 - 521

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Citation Number: 4

Abstract

The protolytic cleavage of tricyc10 [2.2. 0.0~~~] hexane (3), tricyclo [3.2. 0.02~'] heptane (lo), methyltricyclo-[3.2. 0.02 v7] heptanes (26), tricyclo [3.3. 0.~ 8] octane (53), and tricyc10 [3.2. 1.02*~] 0ctane (58) in acetic acid and in aqueous dioxane has been investigated. Protonation occurred at a specific site (3, 36b, d, 58) or competitively at two sites (10, 26c, 53), depending on the stability of the incipient carbocations. Product distributions and ...