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Zirconium‐Mediated Conversion of Amides to Nitriles: A Surprising Additive Effect
Author(s) -
Ruck Rebecca T.,
Bergman Robert G.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461064
Subject(s) - nitrile , chemistry , amide , zirconium , chloride , transformation (genetics) , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , gene
Chloride coordination is the key : Dimethylzirconocene reacts with amides to form methylzirconium amide complexes. On heating, in the presence of a chloride source, these compounds are converted into N ‐acylimidozirconocene complexes that react intramolecularly to form the corresponding nitrile compounds (see scheme; Cp=C 5 H 5 ). Mechanistic studies reveal that chloride coordination to zirconium is required for this transformation to occur.