N, N, N', N'-Tetramethylazodicarboxamide (TMAD), A New Versatile Reagent for Mitsunobu Reaction. Its Application to Synthesis of Secondary Amines.

T Tsunoda, J Otsuka, Y Yamamiya, S Itô

Index: Tsunoda, Tetsuto; Otsuka, Junko; Yamamiya, Yoshiko; Ito, Sho Chemistry Letters, 1994 , # 3 p. 539 - 542

Full Text: HTML

Citation Number: 100

Abstract

N, N, N′, N′-Tetramethylazodicarboxamide, TMAD, was found to be more versatile in the Mitsunobu reaction than traditional diethyl azodicarboxylate or recently developed 1, 1′- (azodicarbonyl) dipiperidine, when used in combination with tributylphosphine in benzene. The usefulness of the reagent was demonstrated by the highly efficient two-step synthesis of benzylcrotylamine from N-benzyltrifluoroacetamide.