| Autor: |
Cole, ER, Crank, G, Minh, HTH |
| Zdroj: |
Australian Journal of Chemistry; 1980, Vol. 33 Issue: 3 p527-543, 17p |
| Abstrakt: |
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. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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