Photocycloaddition of Thiocarbonyl Compounds to Multiple Bonds. VII. The Reaction of Thiobenzophenone with Acetylenic Compounds

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概要

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• Photocycloaddition of thiobenzophenone to acetylenic compounds, R–C≡C–R′ (R=COOH, Ph, CH<SUB>2</SUB>OH, and CN; R′=H: R=COOMe; R′=COOMe), affords 1-phenyl-2-thia-1,2-dihydronaphthalene derivatives. The key step to the product is an intra-molecular aromatic substitution of the composite vinylic biradical <B>13</B>. The difference in reactivity of acetylenic and olefinic compounds as well as that between thiobenzophenone and benzophenone are discussed. Ethoxyacetylene does not undergo the reaction. This is interpreted in terms of electronegativity of a radical center in <B>13</B>. It is found that cyanoacetylene reacts with butanethiyl radical in contrast to its olefin analog, acrylonitrile.

• 公益社団法人 日本化学会の論文

著者

• Ohnishi Yutaka

  Sagami Chemical Research Center

• Ohno Atsuyoshi

  Sagami Chemical Research Center

• Koizumi Tamotsu

  Sagami Chemical Research Center

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