G. Papageorgiou, J. Corrie
Mar 17, 1997
Citations
0
Influential Citations
44
Citations
Journal
Tetrahedron
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.