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Activation of nitriles by hydrogen bonding in cycloadditions with nitrile oxides
Author(s) -
Corsaro Antonino,
Chiacchio Ugo,
Caramella Pierluigi,
Purrello Giovanni
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210403
Subject(s) - benzonitrile , chemistry , nitrile , cycloaddition , hydrogen bond , solvent , hydrogen , organic chemistry , photochemistry , medicinal chemistry , molecule , catalysis
Abstract The dipolarophilic activity of aromatic nitriles in cycloaddition with benzonitrile oxides is remarkably enhanced by ortho ‐acylamino substituents. The activation depends upon the solvent and can be ascribed to a hydrogen bond which assists cycloaddition.