Tetrahedron

[3+ 2]-cycloadditions of 1-Aza-2-azoniaallene cations to multiple bonds

Q Wang, A Amer, S Mohr, E Ertel, JC Jochims

Index: Wang, Quanrui; Amer, Atef; Mohr, Susanne; Ertel, Eveline; Jochims, Johannes C. Tetrahedron, 1993 , vol. 49, # 44 p. 9973 - 9986

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Citation Number: 49

Abstract

Hydrazones of ketones 1, are transformed into 1-chloroalkylazo compounds, 2, which react with Lewis acids to give transient 1-aza-2-azoniaallene salts, 3. The cations 3 react with with acetylenes, olefins, isocyanates, carbodiimides, and nitriles under [3+ 2]-cycloadditions. The cycloadducts undergo consecutive reactions, eg [1, 2]-shifts of alkyl groups.