The Reaction of Alkyl Halides with Mercuric Thiocyanate

Abstract

Abstract The reaction of secondary and tertiary alkyl halides with mercuric thiocyanate in less-polar solvents e.g., n-hexane, di-n-butyl ether, and 1,2-dichloroethane) was found to afford predominantly N-alkylation products, alkyl isothiocyanates, in contrast to the reaction with potassium salt in DMF. Especially, from t-butyl bromide, α-phenethyl bromide and benzhydryl chloride, the corresponding pure isothiocyanates were obtained in good yields. A most probable reaction mechanism is suggested, based on the relative rate data, the stereochemical result of the reaction with optically active α-phenethyl bromide, and the well-known catalytic effect of silver or mercury salt in SN1 reaction.