Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

S Auricchio, C Magnani…

Index: Auricchio, Sergio; Magnani, Caterina; Truscello, Ada M. European Journal of Organic Chemistry, 2002 , # 14 p. 2411 - 2416

Full Text: HTML

Citation Number: 0

Abstract

Abstract 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 ...