Free-radical reaction of cyanogen bromide with alkanes

Abstract

The photolysis of cyanogen bromide with cyclohexane yielded cyclohexyl bromide, hydrogen cyanide, and small amounts of cyanogen, while the benzoyl-peroxide-promoted reactions of cyanogen bromide with various alkanes yielded approximately equal amounts of alkyl bromides and alkyl cyanides, often in high yields. Both hydrogen cyanide and hydrogen bromide were shown to react with benzoyl peroxide and an added hydrocarbon to yield the corresponding alkyl cyanide and alkyl bromide. Possible reaction mechanisms for these reactions are discussed.