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

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

Yasuharu Yoshimi 1,* email, Shota Hayashi 1 , Keisuke Nishikawa 1 , Yoshiki Haga 1 , Kousuke Maeda 1 , Toshio Morita 1 , Tatsuya Itou 2,* email, Yutaka Okada 2 , Nobuyuki Ichinose 3 email and Minoru Hatanaka 4 email
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; in revised form: 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

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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.

AMA 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(4):2623-2630.

Chicago/Turabian Style

Yoshimi, Yasuharu; Hayashi, Shota; Nishikawa, Keisuke; Haga, Yoshiki; Maeda, Kousuke; Morita, Toshio; Itou, Tatsuya; Okada, Yutaka; Ichinose, Nobuyuki; Hatanaka, Minoru. 2010. "Influence of Solvent, Electron Acceptors and Arenes on Photochemical Decarboxylation of Free Carboxylic Acids via Single Electron Transfer (SET)." Molecules 15, no. 4: 2623-2630.

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