Oxidative trifluoroacetamidation of (1E,3E)-1,4-diphenylbuta-1,3-diene and 1,1,4,4-tetraphenylbuta-1,3-diene

Abstract

Reactions of trifluoroacetamide with (1E,3E)-1,4-diphenylbuta-1,3-diene and 1,1,4,4-tetraphenylbuta-1,3-diene in the oxidative system t-BuOCl–NaI have been studied. The reaction with (1E,3E)-1,4-diphenylbuta-1,3-diene afforded three products, N,N′-(phenylmethylene)bis(trifluoroacetamide), 3-chloro-4-iodo- 2,5-diphenyl-1-(trifluoroacetyl)pyrrolidine, and trifluoro-N-[(3E)-2-hydroxy-1,4-diphenylbut-3-en-1-yl]acetamide, with a high overall yield. 1,1,4,4-Tetraphenylbuta-1,3-diene failed to react with trifluoroacetamide.