Studies in the dithiocarbamate series. Part I. Synthesis and decomposition of some 4-hydroxybenzyl dithiocarbamates

Abstract

Interaction of carbon disulphide with either N-(4-hydroxy-3,5-di-t-butylbenzyl)piperidine or a mixture of piperidine, paraformaldehyde, and 2,6-di-t-butylphenol gave 4-hydroxy-3,5-di-t-butylbenzyl piperidine-1-carbodithioate. Decomposition of this compound yielded a piperidine-1-carbodithioate salt, 3,3′,5,5′-tetra-t-butylstilbene-4,4′-quinone, 1,2-bis-(4-hydroxy-3,5-di-t-butylphenyl)ethane, 4-hydroxy-3,5-di-t-butylbenzyl alcohol, 4-hydroxy-3,5-di-t-butylbenzaldehyde, and 4-hydroxy-3,5-di-t-butylbenzyl acetate, the products being dependent on the decomposition conditions. 4-Hydroxy-α-methyl-3,5-di-t-butylbenzyl piperidine-1-carbodithioate, synthesised from carbon disulphide and N-(4-hydroxy-α-methyl-3,5-di-t-butylbenzyl)piperidine, on decomposition yielded 2,6-di-t-butyl-4-vinylphenol, 4-ethylidene-2,6-di-t-butylcyclohexa-2,5-dienone, and 4-hydroxy-α-methyl-3,5-di-t-butylbenzyl methyl ether. 4-Hydroxy-αα-dimethyl-3,5-di-t-butylbenzyl piperidine-1-carbodithioate, synthesised analogously, on decomposition yielded corresponding products. Mechanisms are proposed to explain the formation of the decomposition products.