Tetrahedron

Biomimetic building-up of the carbamic moiety: the intermediacy of carboxyphosphate analogues in the synthesis of N-aryl carbamate esters from arylamines and …

M Aresta, C Berloco, E Quaranta

Index: Aresta, Michele; Berloco, Chlara; Quaranta, Eugenio Tetrahedron, 1995 , vol. 51, # 29 p. 8073 - 8088

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Citation Number: 49

Abstract

The reaction of aromatic amines with dimethyl carbonate (DMC) or diphenyl carbonate (DPC) in the presence of organo-phosphorus acids [Ph2P (O) OH (1);(PhO) 2P (O) OH (2);(BuO) 2P (O) OH/(BuO) P (O)(OH) 2 equimolar mixture (3)] affords carbamate esters, ArNHC (O) OR (R= Me, Ph) with high selectivity. The catalytic role played by the P-acid has been investigated and rationalized in terms of a reaction mechanism involving the ...