Anionic [3, 3],[2, 3] and [1, 2] rearrangements of aliphatic and aromatic acyl hydrazines with N N bond cleavage

Y Endo, T Uchida, K Shudo

Index: Endo, Yasuyuki; Uchida, Takuya; Shudo, Koichi Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2113 - 2116

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Citation Number: 18

Abstract

N-Acyl-N′-phenylhydrazines rearrange under basic conditions to afford o-aminophenyl- acetamides. This reaction can be rationalized in terms of [3, 3] sigmatropic shifts of enolized intermediates. The Sommelet-Hauser-type and Stevens-type rearrangements of both aromatic and aliphatic acylhydrazines compete with the [3, 3] rearrangement.