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 ...
