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Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack
Author(s) -
Auricchio Sergio,
Magnani Caterina,
Truscello Ada M.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200207)2002:14<2411::aid-ejoc2411>3.0.co;2-n
Subject(s) - carbocation , chemistry , nitrile , intramolecular force , lewis acids and bases , medicinal chemistry , reaction mechanism , organic chemistry , catalysis
Reactions between nitrile oxides and benzylic carbocations are described. Different results were obtained when the carbocations were generated from the corresponding chlorides with different Lewis acids, with addition products such as benzoxazines, oximes, and amides being produced. Primary, secondary, and tertiary carbocations showed different reactivities. The product ratios strongly depended on the substituents on the aromatic ring of the benzylic carbocations. Evidence for the proposed mechanism is reported. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)