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Molecules 2010, 15(4), 2623-2630; doi:10.3390/molecules15042623

Influence of Solvent, Electron Acceptors and Arenes on Photochemical Decarboxylation of Free Carboxylic Acids via Single Electron Transfer (SET)

1
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan
2
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, 1-1-1 Noji-Higashi, Kusatsu 525-8577, Japan
3
Department of Chemistry and Materials Technology, Kyoto Institue of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
4
Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan
*
Authors to whom correspondence should be addressed.
Received: 15 March 2010 / Revised: 2 April 2010 / Accepted: 7 April 2010 / Published: 12 April 2010
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Abstract

Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene in the presence of various electron acceptors such as 1,2-, 1,3-, and 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, and 1,4-dicyanonaphthalene. The decarboxylation reaction was influenced by the arenes, electron acceptors, and solvent. The best result was achieved by the photoreaction using biphenyl and 1,4-dicyanonaphthalene in aqueous acetonitrile.
Keywords: photochemical decarboxylation; single electron transfer; free carboxylic acid photochemical decarboxylation; single electron transfer; free carboxylic acid
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MDPI and ACS Style

Yoshimi, Y.; Hayashi, S.; Nishikawa, K.; Haga, Y.; Maeda, K.; Morita, T.; Itou, T.; Okada, Y.; Ichinose, N.; Hatanaka, M. Influence of Solvent, Electron Acceptors and Arenes on Photochemical Decarboxylation of Free Carboxylic Acids via Single Electron Transfer (SET). Molecules 2010, 15, 2623-2630.

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