摘要：

THE formation of stable alkylammonium thiolate salts from the reaction of benzenethiol with p -, sec - and tert -aliphatic amines was first observed by Gordy and Stanford 1 and further substantiated by Grillot and Brooks 2 . Subsequent work has demonstrated that: ( a ) the formation of alkylammonium thiolates from the reaction or aromatic and arakyl thiols with aliphatic amines is a general reaction; ( b ) that aliphatic amines catalyse the oxidation of thiols by molecular oxygen in hydrocarbon solvents 3 . The latter suggests that the active species in these oxidations is the thiol anion ( R S ). Recent investigations in these laboratories have demonstrated that dipolar solvents markedly accelerate the base-catalysed oxidation of thiols 4 . This finding coupled with the foregoing results suggested that tetramethylguanidine (TMG) would be capable of functioning simultaneously as both a solvent and a base for thiol oxidations. This was found to be true.

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