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The site‐selectivity of cycloadditions of nitrile oxides to β‐aminocinnamonitriles. A remarkable solvent dependence
Author(s) -
Corsaro Antonino,
Chiacchio Ugo,
Perrini Giancarlo,
Caramella Pierluigi,
Purrello Giovanni
Publication year - 1985
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.5570220336
Subject(s) - chemistry , nitrile , acceptor , hydrogen bond , solvent , selectivity , photochemistry , hydrogen , solvent effects , organic chemistry , molecule , catalysis , physics , condensed matter physics
Cycloadditions of nitrile oxides to N ‐mono and unsubstituted β‐aminocinnamonitriles are remarkably affected by the hydrogen acceptor ability of the solvent. Addition to C N bond predominates in non and weak hydrogen bond acceptor solvents because of the assistance of favourable hydrogen bonding effects. In strong hydrogen bond acceptor solvents the assistance is fully relieved and the regular addition to C C bond becomes prevalent.