Reduction of propargylic chlorides with tri-n-butyltin hydride. The ambident behavior of propargylic radicals

RM Fantazier, ML Poutsma

Index: Fantazier,R.M.; Poutsma,M.L. Journal of the American Chemical Society, 1968 , vol. 90, p. 5490 - 5498

Full Text: HTML

Citation Number: 36

Abstract

Abstract: Ten substituted propargylic chlorides (1-10) have been reduced by tri-n-butyltin hydride to produce in each case a mixture of the corresponding acetylene and isomeric allene. Initiation and inhibition studies for a typical case, 3-chloro-3-methyl-1-butyne (3), indicated a free-radical reaction course. The initial, kinetically controlled acetylene-allene ratios are thus discussed in terms of the behavior of the series of substituted propargylic ...