PREPARATION AND USE OF SOME HYDROCARBON DIANIONS IN SYNTHESIS (PENTADIENE, HEXADIENE, ALKYL, HALIDE, BROMIDE).

Abstract

One new dianion was prepared and many alkylation and oxidation reactions of this new dianion and several known dianions were carried out. These reactions provide the best synthetic routes to most of the compounds prepared. More specifically, many oxidation products were obtained when 3-methyl-1,4-pentadiene dianion was treated with alkyl bromides. A quantitative yield of substitution product was obtained by reacting this dianion with trimethylsilyl chloride. New compounds obtained by treating this dianion with 1,2-dichloroethane are shown below: The dianion shown below was prepared from 2,5-dimethyl-1,5-hexadiene and Lochmann's base. Many different 2,5-disubstituted 1,5-hexadienes and related compounds were made by treating this dianion with alkyl halides, sulfates and alkyl (alpha),(omega)-dihalides. Attempts to make a cyclic hexapyridyl by treating 2-methyleneallyl dianion with 6,6'-dicyano-2,2'-dipyridyl (see below) apparently failed.