Heterocyclic synthesis via the reaction of nitrones and hydroxylamines with substituted allenes

…, WH Bullock, DN Kline, J Perumattam

Index: Padwa, Albert; Bullock, William H.; Kline, Donald N.; Perumattam, John Journal of Organic Chemistry, 1989 , vol. 54, # 12 p. 2862 - 2869

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Citation Number: 65

Abstract

The 1, 3-dipolar cycloaddition of N-methyl-and N-phenyl-C-phenylnitrone with several allenes has been investigated. In the case of dimethylallene, a 1: l mixture of products derived from dipolar cycloaddition across both n-bonds was obtained. The formation of a benzazepinone derivative from this reaction was rationalized in terms of a subsequent rearrangement of a transient 5-methyleneisoxazolidine. In contrast to this result, ...