Fragmentation reactions promoted by cyanogen bromide

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Abstract
The fragmentation of α-4-dimethylamino-3-methyl-1,2-diphenylbutan-2-ol to cis H/Ph 3-methyl-1,2-diphenylprop-2-ene, normally induced by treating the corresponding 2-chloro derivative with a base, also results when the alcohol itself is treated with cyanogen bromide; related γ-hydroxy acyclic tertiary amines similarly undergo fragmentation in this reaction. In contrast, cyclic analogues such as β-1,3-dimethyl-4-phenyl-4-piperidinol are not cleaved by cyanogen bromide (corresponding N-cyano derivatives are formed in low yield) even though β-4-chloro-1,3-dimethyl-4-phenylpiperidine is fragmented by potassium cyanide to trans H/Ph 5(N-cyanomethyl-N-methylamino)-3-phenylpent-2-ene.

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