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 | Zendy

Alcaraz Gilles | Zendy; Wecker Ulrich | Zendy; Baceiredo Antoine | Zendy; Dahan Françoise | Zendy; Bertrand Guy | Zendy

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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.

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