Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one

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Title: Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one
Authors: Batanero, Belén | Barba, Fructuoso | Barba, Isidoro | Elinson, Michail N.
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: 1,2-Quinones cathodic reduction | Electrochemical Baeyer–Villiger/Dakin-type reaction | Electron-transfer | Superoxide anion | Aromatic carbolactones
Knowledge Area: Química Orgánica
Issue Date: 1-Jan-2014
Publisher: Elsevier
Citation: Tetrahedron Letters. 2014, 55(1): 82-85. doi:10.1016/j.tetlet.2013.10.123
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.
Sponsor: This work was supported by the Spanish Ministry of Science and Education through B. Batanero I3 program financial support.
ISSN: 0040-4039 (Print) | 1873-3581 (Online)
DOI: 10.1016/j.tetlet.2013.10.123
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas

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