Author:
Píšová Milena,Souček Milan
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 key intermediate.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
3 articles.
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