Batanero, Belén, Barba, Fructuoso, Barba, Isidoro, Elinson, Michail N.
Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one
Tetrahedron Letters. 2014, 55(1): 82-85. doi:10.1016/j.tetlet.2013.10.123
URI: http://hdl.handle.net/10045/37721
DOI: 10.1016/j.tetlet.2013.10.123
ISSN: 0040-4039 (Print)
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–Villiger/Dakin-type reaction, Electron-transfer, Superoxide anion, Aromatic carbolactones
Elsevier
info:eu-repo/semantics/article