75080-63-6Relevant academic research and scientific papers
Oxidations with Lead Tetraacetate. II. Oxidations of 2,2-Disubstituted 1,3-Benzodioxoles
Cole, Edward R.,Crank, George,Minh, H. T. Hai
, p. 527 - 543 (2007/10/02)
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 compuonds 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 ο-quinone formation is discussed and is postulated to occur via a tetraacetoxy intermediate.The 5-acetoxy derivatives and the ο-quinones, by hydrolysis and reduction respectively, serve as sources of 5-hydroxy and 5,6-dihydroxy benzodioxoles.
