The Journal of Organic Chemistry

Preparation of 2-Substituted 1, 3, 5-Hexatrienes

CW Spangler, GF Woods

Index: Spangler,C.W.; Woods,G.F. Journal of Organic Chemistry, 1963 , vol. 28, p. 2245 - 2248

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Citation Number: 8

Abstract

A recently reported method of preparation of 1, 3, 5-hexatriene1 has now been utilized for the synthesis of 2-chloro-, 2-bromo-, and 2-methyl-1, 3, 5-hexatriene. The synthesis consists of (1) reaction of an allylic Grignard reagent with the appropriate unsaturated aldehyde,(2) conversion of the resulting dienol to a dienic bromide by means of phosphorus tribromide,(3) reaction of the dienic bromide with N, N-dimethylbenzylamine to yield a quaternary ...