Liquid-phase bromination of bromobutane: variation of the ratio of 1,2- to 1,3-dibromobutanes produced

Abstract

The liquid-phase bromination of 1-bromo- and 1-chloro-butane has been studied using t-butyl hypobromite and bromine oxide as brominating agents. These reagents give a mixture of all four dibromobutanes from 1-bromobutane with less 1,2- than 1,3-dibromobutane, in contrast to bromination with molecular bromine which gives mainly 1,2-dibromobutane. The significance of these observations, taken together with the data obtained from the halogenation of 1-chlorobutane is discussed with respect to anchimeric assistance and the effect of hydrogen bromide on the course of bromination.