Oxidative cleavage of tin-tin bonds in hexaalkyldistannane with several 1,4-benzoquinones. Detection of the semiquinone radicals and 4-(trialkylstannoxy)phenoxyl radicals by ESR spectroscopy.

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概要

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• The mechanism of the oxidative cleavage of tin–tin bonds in hexamethyldistannane (Me<SUB>3</SUB>SnSnMe<SUB>3</SUB>) and hexabutyldistannane (Bu<SUB>3</SUB>SnSnBu<SUB>3</SUB>) with several 1,4-benzoquinones was investigated. Chlorine-substituted 1,4-benzoquinones exerted higher reactivity, implying that the electron-acceptability of quinone is a factor governing the reaction. Stoichiometric treatments of chloranil with the distannanes ruled out the alleged isolation of the free radical, 4-(trimethylstannoxy)phenoxyl radical, reported by Gornwell <I>et al.</I> The final products were not the free radical entity but normal compounds, 1,4-bis(trimethylstannoxy)benzenes. Measurements of ESR spectra revealed the formation of the semiquinone radical anions and the subsequent formation of 4-(tributylstannoxy)phenoxyl radicals as reactive intermediates in the reaction pathway.

• 公益社団法人 日本化学会の論文

著者

• Fujita Hideo

  Department Of Aeronautics University Of Tokyo

• Kozima Sinpei

  Department Of Natural Environment Sciences Faculty Of Integrated Human Studies Kyoto University

• Kobayashi Kazuko

  Department Of Cell Chemistry Okayama University Graduate School Of Medicine And Dentistry

• HITOMI Torazo

  Department of Chemistry, College of Liberal Artrs and Sciences, Kyoto Univeristy

• Kobayashi Kazuhiko

  Department of Chemistry, Faculty of Science, Kanazawa University

• Kawanisi Mituyoshi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Kozima Sinpei

  Department of Chemistry, College of Liberal Arts and Sciences, Kyoto University

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