Reactions of lead tetraacetate. II. Formation of carbamic acid esters from primary carboxamides

Abstract

Treatment of primary carboxamides with lead tetraacetate in benzene-alcohol mixtures or neat alcohol affords a convenient, flexible, and efficient method for the preparation of N-substituted carbamic acid esters. The reaction is applicable to amides and alcohols of a wide range of structural types including compounds containing oleflnic, ester, aromatic, and other reactive functions. The reaction mechanism appears to involve intermediate formation of isocyanates.