T. Tsunoda, Hirofumi Yamamoto, Kayo Goda
Apr 1, 1996
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron Letters
Abstract
Abstract p-Toluenesulfonamide, which is known to form phosphine imides under Mitsunobu conditions, was shown to be alkylated in the presence of cyanomethylenetributylphsphorane to give N-substituted sulfonamides in excellent yields. The reaction can be applied to the synthesis of symmetrical and unsymmetrical N,N-disubstituted amides. When coupled with the desulfurization reactions, the reaction provides a new versatile synthetic route to primary and secondary amines from ammonia.