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Synthesis of a 2 H ‐Azirine by [1 + 2] Cycloaddition of a Phosphinocarbene with a Nitrile and Its Ring‐Expansion to a 1,2λ 5 ‐Azaphosphete
Author(s) -
Alcaraz Gilles,
Wecker Ulrich,
Baceiredo Antoine,
Dahan Françoise,
Bertrand Guy
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199512461
Subject(s) - azirine , benzonitrile , nitrile , dichloromethane , carbene , ring (chemistry) , chemistry , medicinal chemistry , catalysis , ruthenium , cycloaddition , organic chemistry , solvent
A new type of carbene reaction is observed with the stable phosphinocarbene 1 . It reacts with benzonitrile to give the 2 H ‐azirine 2 , which in dichloromethane is converted into the 1,2λ 5 ‐azaphosphete 3 after addition of a catalytic amount of dichloro( p ‐cymene)ruthenium( II ). R = ( c ‐C 6 H 11 ) 2 N.