MITSUNOBU-TYPE ALKYLATION OF P-TOLUENESULFONAMIDE - A CONVENIENT NEW ROUTE TO PRIMARY AND SECONDARY-AMINES

p-Toluenesulfonamide, which is known to form phosphine imides under Mi tsunobu conditions, was shown to be alkylated in the presence of cyano methylenetributylphsphorane to give N-substituted sulfonamides in exce llent yields. The reaction can be applied to the synthesis of symmetri cal and unsymmetrical N,N-disubstituted amides. When coupled with the desulfurization reactions, the reaction provides anew versatile synthe tic route to primary and secondary amines from ammonia. Copyright (C) 1996 Elsevier Science Ltd