Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies

K Mizuno, N Ichinose, T Tamai…

Index: Mizuno, Kazuhiko; Ichinose, Nobuyuki; Tamai, Toshiyuki; Otsuji, Yoshio Journal of Organic Chemistry, 1992 , vol. 57, # 17 p. 4669 - 4675

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Citation Number: 43

Abstract

Nitrogen oxide (NO) has a radical character and can be used as a radical trapping agents1 An elegant use of this property of NO in organic synthesis is the photolysis of alkyl nitrites, in which an unactivated CH group is nitrosated regioselectively. This reaction occurs via the photolytic cleavage of an alkyl nitrite to generate an alkoxy1 radical and NO. Intramolecular hydrogen abstraction from the alkyl group by the alkoxy1 radical in a 1, 5-hydrogen shift ...