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
Full Text: HTML
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.
Related Articles:
Synthesis of indoles via alkylidenation of acyl hydrazides
[Hisler, Kevin; Commeureuc, Aurelien G.J.; Zhou, Sheng-ze; Murphy, John A. Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3290 - 3293]
Synthesis and Some Reactions of Triphenylphosphinamino-and (β-N-Disubstituted amino) imines
[Zimmer,H.; Singh,G. Journal of Organic Chemistry, 1964 , vol. 29, p. 1579 - 1581]