Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of Heteroaromaticity. XXIV. 1,3-Dipolar Cycloaddition of C-(5-Nitro-2-furyl)-N-phenylnitrone
Tadashi SasakiToshiyuki YoshiokaIwao Izure
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1968 Volume 41 Issue 12 Pages 2964-2969

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Abstract

C-(5-Nitro-2-furyl)-N-phenylnitrone (I) was prepared from 5-nitro-2-furfural and phenylhydroxylamine in an 80% yield. The 1,3-dipolar cycloaddition reactions of I with various olefins were carried out, and the corresponding 5-substituted isoxazolidine derivatives were obtained. The structual elucidation of these products was made on the basis of the nmr spectral data. Several observations support the theory that these reactions proceed via a concerted one-step process.

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