Electron-transfer reduction of .ALPHA.-substituted ketones and 1,2-diketones with benzenethiol mediated by iron polyphthalocyanine.

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概要

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• Iron polyphthalocyanine (Fe-poly PC) has been found to act as an electron-transfer reagent in the reductions of α-substituted ketones, α-bromodeoxybenzoin (<B>1a</B>), 2-bromopropiophenone (<B>1b</B>), α,α-bis(phenylthio)deoxybenzoin (<B>4</B>), and 1,2-diketones, benzil (<B>5</B>) and 4,5-octanedione (<B>8</B>), with benzenethiol. The α-bromo ketones (<B>1a</B> and <B>1b</B>) have been debrominated to their parent ketones. <B>4</B> has been reduced to α-(phenylthio)deoxybenzoin and deoxybenzoin <I>via</I> the cleavage of the carbon-sulfur bond, and <B>5</B> and <B>8</B> to the corresponding α-hydroxy ketones. The ability of Fe-poly PC to perform these reactions is superior to that of iron phthalocyanine (Fe-PC), particularly those reactions in dry benzene. The catalytic action of Fe-poly PC and Fe-PC becomes evident when methanol or 80 vol % aqueous methanol is used as solvent. Furthermore, the reductions of related compounds by the Fe-poly PC-benzenethiol system are described.

• 公益社団法人 日本化学会の論文

著者

• Inoue Hiroo

  Department Of Applied Chemistry College Of Engineering Osaka Prefecture University

• NAGATA Tadashi

  Department of Computer Science and Communication Engineering,Faculty of Engineering,Kyushu Universit

• Imoto Eiji

  Department of Applied Chemistry College of Engineering The University of Osaka Prefecture

• HATA Hiroyuki

  Department of Agricultural Chemistry, Kyoto University

• Nagata Tadashi

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

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