Organosilicon chemistry. Part X. The reaction of diazomethyltrimethylsilane with trifluoroacetonitrile and cyanogen halides to give triazoles

Abstract

Reaction of diazomethyltrimethylsilane with trifluoroacetonitrile at room temperature gives 4-trifluoromethyl-2-trimethylsilyl-1,2,3-triazole in high yield, while reaction with cyanogen chloride or cyanogen bromide yields mixtures of the 4-halogeno-2-trimethylsilyl-1,2,3-triazole and an isomeric product, probably the 2-halogeno-2-(N-trimethylsilylimino)diazoethane. Hydrolysis of the 1 : 1 adducts gives, in each case, the corresponding 4-substituted-1,2,3-triazole in good yield.