Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one |
| |
Authors: | Belen Batanero Fructuoso Barba Isidoro Barba Michail N. Elinson |
| |
Affiliation: | 1. Department of Organic Chemistry, University of Alcala, 28871 Alcalá de Henares (Madrid), Spain;2. Department of Organic Chemistry, University of Alicante, Ap. 99, 03080 Alicante, Spain;3. N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, 119991 Moscow, Russia |
| |
Abstract: | In the present Letter several carbolactones (oxidative products) are obtained under aprotic cathodic conditions in the preparative scaled electrolysis of 1,2-quinones in a divided electrochemical cell and in the presence of oxygen. When 9,10-phenanthrenequinone is reduced 6H-dibenzo[b,d]pyran-6-one and [1,1′-biphenyl]-2,2′-dicarboxylic acid are obtained as major products. In the reduction of 1,2-naphthoquinone, 2-benzopyran-1(1H)-one, and 2-(2-carboxyethenyl)-benzoic acid were formed as main products. The proposed mechanism to explain the formation of these and other products, that involves an electron-transfer reaction to the oxygen in air, is now discussed. |
| |
Keywords: | 1,2-Quinones cathodic reduction Electrochemical Baeyer&ndash Villiger/Dakin-type reaction Electron-transfer Superoxide anion Aromatic carbolactones |
本文献已被 ScienceDirect 等数据库收录! |
|