ADDITION OF TRICHLOROMETHYL RADICALS TO ALKENYLSILANES

Dibenzoyl peroxide catalyzed addition of bromotrichloromethane to various types of vinyl- and w-alkenyl-silanes have been investigated. Six new addition compounds have been prepared and characterized. It has been found that the reactivity of the double bond in the series of R(CH3)2SiCH=CH2, where R = Me, Et, i-Pr, and t-Bu, toward addition of the trichloromethyl radical is governed by the Taft steric factor, E., of R, while the reactivity in the series of Cln(CH3)3-nSiCH=CH2 is approximately related to the inductive effect. In the series of (CH3)3Si(CH2)nCH=CH2, where n = 0-4, the reactivity reaches a maximum when n = 1. Factors influencing the reactivity have been discussed. © 1969, American Chemical Society. All rights reserved.