Abstract
The oxidation of
2,2-disubstituted 1,3-benzodioxoles by lead tetraacetate proceeds readily to
give 5-acetoxy and 5,6-dione derivatives as main products. 5,6-Diacetoxy
compounds and 5-carboxy derivatives are found in some instances as minor
products. Oxidation of benzodioxoles substituted at the 5 and 6 positions with methoxyl groups or with a second dioxole ring results in
oxidative loss of the dioxole ring. Relative effects of these substitutions on
reactivity have been evaluated. The mechanism of o-quinone formation is
discussed and is postulated to occur via a tetraacetoxy intermediate. The
5-acetoxy derivatives and the o-quinones, by hydrolysis and reduction
respectively, serve as sources of 5-hydroxy and 5,6-dihydroxy benzodioxoles.
Cited by
21 articles.
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