Chemistry of organoditins II. The free radical chain reaction between n-chlorosuccinimide and hexaalkylditins

Abstract

The reaction of N -chlorosuccinimide with hexaalkylditins has been examined. The reaction has been found to be subject to catalysis by molecular oxygen, and to inhibition by galvinoxyl. A free radical chain mechanism is proposed in which one propagating step involves attack upon the ditin by N -succinimidyl radicals, and another involves attack upon the chlorine atom of the N -chlorosuccinimide molecule by organotin radicals. Evidence is also presented that dimethylamino radicals from decomposition of 1,1,4,4-tetramethyl-2-tetrazine participate in a homolytic displacement upon the tin radical of hexamethylditin. On the other hand, the trimethyltin radicals do not appear to attack the nitrogen of the tetramethylhydrazine.