Mechanistic definition of trimethylstannylation of 1, 4-dihalobicyclo [2.2. 1] heptanes: bridgehead nucleophilic substitution mediated by the intermediacy of radicals, …

W Adcock, H Gangodawila

Index: Adcock, William; Gangodawila, Hemakanthi Journal of Organic Chemistry, 1989 , vol. 54, # 26 p. 6040 - 6047

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Citation Number: 20

Abstract

A series of 1, 4-dihalobicyclo [2.2. l] heptanes (2; X= Y= halogens) have been synthesized, characterized, and treated with (trimethylstanny1) lithium (Me, SnLi) in the absence and presence of tert-butylamine (TBA). The product distributions of these reactions have been established by'% and*'% n NMR spectroscopy and vapor-phase chromatographic analyses. The results clearly indicate that a polar mechanism involving the formation of a carbanion ...