Rearrangements in the cerium (IV) and manganese (III) oxidations of substituted naphthalenes and the NIH shift mechanism

MV Bhatt, M Periasamy

Index: Bhatt, M. Vivekananda; Periasamy, Mariappan Tetrahedron, 1994 , vol. 50, # 11 p. 3575 - 3586

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Citation Number: 11

Abstract

Ceric ammonium sulphate oxidation of 1-md 1, 4-disubstituted naphthalenes gives 2-and/or 2, 3-disubstituted 1, 4-naphthoquinones through migration of substituents (D, Br, Ph). Similar rearrangements are also observed in the manganese (III) oxidation and also in the anodic oxidation of these substrates. The results are consistent with the proposal that these oxidations go through the formation of radical cation followed by reaction with H2O and ...