N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENTFOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES

Authors
TSUNODA T OTSUKA J YAMAMIYA Y ITO S
Citation
T. Tsunoda et al., N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENTFOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES, Chemistry Letters, (3), 1994, pp. 539-542
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
3
Year of publication
1994
Pages
539 - 542
Database
ISI
SICI code
0366-7022(1994):3<539:N(ANVR>2.0.ZU;2-D
Abstract
N,N,N,N'-Tetramethylazodicarboxamide, TMAD, was found to be more versa tile in the Mitsunobu reaction than traditional diethyl azodicarboxyla te or recently developed 1,1'-(azodicarbonyl)dipiperidine, when used i n combination with tributylphosphine in benzene. The usefulness of the reagent was demonstrated by the highly efficient two-step synthesis o f benzylcrotylamine from N-benzyltrifluoroacetarmide.