Intermediates formed in the reaction of benzenethiol or t-butylthio-benzene with ethyl benzoylacetate in polyphosphoric acid.

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概要

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• The reaction of benzenethiol with ethyl benzoylacetate in polyphosphoric acid (PPA) at low temperature gave mainly ethyl 3-phenyl-3,3-bis(phenylthio)propionate <B>8</B> as an intermediate in the synthesis of thioflavones, while that from <I>t</I>-butylthiobenzene under similar conditions gave ethyl 3-(phenylthio)cinnamate <B>7</B> as a major product and many by-products. The reaction constant for intramolecular cyclic condensation of <B>7</B> in 98% sulfuric acid was −0.46 and −0.54 using Hammett substituent constants, σ<SUB>m</SUB> and σ<SUB>m</SUB><SUP>+</SUP>, respectively. It is suggested that the increase of electron density at the ring closure site of the benzenethiol moiety of <B>7</B> promotes this ring closure reaction.

• 公益社団法人 日本化学会の論文

著者

• Nakazumi Hiroyuki

  Department Of Advanced Materials Science Graduate School Of Engineering Osaka Prefecture University

• Watanabe Shigeru

  Deparment Of Surgery Tokyo Seamen's Insurance Hospital

• Kitao Teijiro

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

• Watanabe Shigeru

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

• Kitaguchi Tohru

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

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• Intermediates formed in the reaction of benzenethiol or t-butylthio-benzene with ethyl benzoylacetate in polyphosphoric acid.

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