Studies in the dithiocarbamate series. Part II. The reaction of substituted N-benzylpiperidines with carbon disulphide

Abstract

A series of substituted N-benzylpiperidines has been prepared, and their reaction with carbon disulphide studied. When the benzyl group possesses a 4-hydroxy-substituent together with 3,5-substituents such as alkyl and methoxy-the reaction leads to dithiocarbamate formation by ‘ insertion’ of carbon disulphide between the benzylic carbon atom and nitrogen. A three-stage mechanism is proposed, one stage involving the formation of a p-quinone methide as a transient intermediate. An alternative two-stage mechanism is considered but shown to be less likely.