The silver(II)- and manganese(III)-mediated radical reactions of 2-substituted-l, 4-naphthoquinones are described. Acyl radicals generated by the oxidative decarboxylation of αketo acids with silver(I) nitrate and persulfate undergo efficient radical addition to the C=C bond of 2-(1-hydroxyalkyl)-1, 4-naphthoquinones and 2-(1-amidoalkyl)-1, 4naphthoquinones. This reaction provides an effective method for the synthesis of naphtho[2, 3-c]furan-4, 9-diones and benzo[f]isoindole-4, 9-diones. In the presence of O2, manganese(III) acetate oxidation of β-keto esters also generates acyl radicals, which then undergo radical addition to 2-(1-amidoalkyl)-1, 4-naphthoquinones, and subsequently, benzo[f]isoindole-4, 9-diones are produced.
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry