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Self-association of trimethylsilyl-3,6-di-tert-butyl-o-semiquinone

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The reaction of sodium 3,6-di-tert-butyl-o-semiquinolate with Me3SiCl in THF leads to the formation of 2-(2′-trimethylsiloxy-3′,6′-di-tert-butylphenoxy)-2-trimethylsiloxy-3,6-di-tert-butylcyclohexadien-3,5-one 1. On the basis of IR and UV spectroscopy and analysis of the reaction products, it has been determined that the cyclohexadiene structure 1 is preserved on heating to moderate temperatures or on reaction with water or HCl, but photolysis leads to its decomposition, and so does reaction with metallic sodium or alkali. A scheme of the process is propounded.

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Institute of Organometallic Chemistry, Russian Academy of Sciences, 603600 Nizhnii Novgorod. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2385–2389, October, 1992.

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Abakumov, G.A., Bayushkin, P.Y. & Filippova, E.I. Self-association of trimethylsilyl-3,6-di-tert-butyl-o-semiquinone. Russ Chem Bull 41, 1871–1874 (1992).

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  • di-tert-butyl-substituted oxyphenoxylradicals
  • self-associates
  • trimethylsilyl-o-semiquinone
  • cyclohexadiene structures
  • geminal recombination reactions