Nucleophilic substitution in 1-substituted 3-iodobicyclo [1.1. 1] pentanes. A new synthetic route to functionalized bicyclo [1.1. 1] pentane derivatives

JL Adcock, AA Gakh

Index: Adcock, James L.; Gakh, Andrei A. Journal of Organic Chemistry, 1992 , vol. 57, # 23 p. 6206 - 6210

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Citation Number: 19

Abstract

Nucleophilic substitution of the iodine in 1-substituted 3-iodobicyclo [lll] pentanes [R= I (l), CF3 (2)] was investigated. The results of the reaction are strongly dependent on the nature of the nucleophile and the substituent. Whereas the trifluoromethyl derivative 2 is found to be inert in the reactions and gave substitution products only with organolithium reagents, the 1, 3-diiodide 1 is much more reactive and affords normal substitution products with nitrogen ...