Abstract

Abstract Carbamoyl derivatives of photolabile benzoins, particularly of 3′,5′-dimethoxybenzoin, are readily prepared via the mixed p-nitrophenyl carbonate of the benzoin. The method is most suitable for secondary amines, since many primary amines exist in varying proportions as the cyclic hydroxyoxazolidinone tautomer. In alkaline solution (0.2 M NaOH) the carbamates of unsymmetrical benzoins are readily equilibrated. Flash photolysis of 3′,5′-dimethoxybenzoin carbamates generates the carbamate anion in a fast heterolytic process and liberation of the amine is controlled by the rate of decarboxylation.

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