A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition

Y Kikugawa, C Tsuji, E Miyazawa, T Sakamoto

Index: Kikugawa, Yasuo; Tsuji, Chiho; Miyazawa, Etsuko; Sakamoto, Takeshi Tetrahedron Letters, 2001 , vol. 42, # 12 p. 2337 - 2339

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Citation Number: 25

Abstract

Previously, we reported the AlCl 3 -mediated heterolytic cleavage of the NO bond of N-phenoxybenzamides that leads to an intramolecular migration of the benzamido group from the oxygen to the ortho position of the phenyl ring. 4 In an extension of this work, we have investigated the reaction of O-arylketoximes (1) with Lewis acids in benzene. We now report that ZrCl 4 -mediated decomposition of 1 leads to an efficient electrophilic intramolecular migration of the imino group from the ...