Homolytic organometallic reactions. Part VIII. Kinetics of the homolytic reaction between N-halogenosuccinimides and tetra-alkyltins

Abstract

N-Halogenosuccinimides react with tetra-alkyltins by a radical chain mechanism to give the corresponding alkyl halides and N-trialkylstannylsuccinimides. Rate constants for the homolytic attack of the succinimidyl radical at the tin centre have been measured, and interpreted in terms of steric hindrance towards the formation of a 5-co-ordinate transition state, and of electronic stabilisation of the displaced radical. Rate constants for the abstraction of chlorine, bromine, or iodine from the corresponding N-halogenosuccinimide by benzyl and propyl radicals have also been determined.