Oxidative rearrangement of o-fuchsone to 2, 2-diphenyl-1, 3-benzodioxol

M Píšová, M Souček

Index: Pisova, Milena; Soucek, Milan Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 12 p. 3318 - 3327

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Citation Number: 2

Abstract

Abstract The photo-decolouration of o-fuchsone is caused by [8+ 2] cycloaddition of singlet oxygen to the quinonoid trienone π-system. The arising 1, 2, 3-trioxanaphthalene undergoes further fragmentations and recyclizations to give 1, 3-benzodioxol. The course of this reaction was investigated using fuchsones I-IV as substrates and hydrogen peroxide and tert- butyl hydroperoxide as oxidants. The thermolabile epoxy ketone XV was identified as the ...