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Paper | Regular issue | Vol 48, No. 9, 1998, pp.1769-1776
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8194
[4π+2σ]-Type Cycloaddition Reactions of Naphtho[b]cyclopropene with C,N-Diphenylnitrones to Form Dihydronaphthoxazines

Shinichi Ando, Junichi Imamura, Atsushi Hattori, Makiko Tajitsu, and Katsuhiro Saito*

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan

Abstract

Reactions of naphtho[b]cyclopropene with C,N-diphenylnitrone derivatives afforded dihydronaphthoxazine derivatives. The reaction is considered to proceed through a [4π + 2σ]-type cycloaddition process via a zwitter ionic intermediate generated by a rupture of the C-C σ-Bond of the three-membered ring of naphtho[b]cyclopropene caused by a nucleophilic attack of tne nitrone.