Volume 23, Issue 13
Preparative Organic Chemistry
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ChemInform Abstract: Anionic (3,3)-Sigmatropic Rearrangement of N-Phenyl-O- acylhydroxylamines to o-Aminophenylacetic Acids.

Y. ENDO

Y. ENDO

Fac. Pharm. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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S. HIZATATE

S. HIZATATE

Fac. Pharm. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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K. SHUDO

K. SHUDO

Fac. Pharm. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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First published: March 31, 1992

Abstract

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ChemInform Abstract

3-Aza-4-oxa(3,3)sigmatropic rearrangement of the N-phenyl-O- acylhydroxylamines (I), (V) and (IX) gives the ortho-substituted derivatives (III), (VI) and (X), together with the corresponding para- substituted products (IV), (VII) and (XI). In the case of the N- benzoylhydroxylamines (V), substantial amounts of the O- methylhydroxylamine (VIII) derived from ester cleavage are obtained.

chemical structure image

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