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Photooxygenolysis of 3,6-di-tert-butyl-o-benzoquinone

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Abstract

The photolysis of 3,6-and 3,5-di-tert-butyl-o-benzoquinones in benzene (λ > 380 nm, inert atmosphere) involves decarbonylation of the compounds to furnish respectively 2,5-and 2,4-di-tert-butylcyclopentadienones. The 2,5-isomer is stable, and the 2,4-di-tert-butylcyclopentadienone suffers a conversion into a Diels-Alder adduct. The participation of oxygen inhibited the decarbonylation and changed the direction of the photolysis: Here the products of the 3,5-di-tert-butyl-o-benzoquinones conversion were a di-tert-butylmuconic anhydride and dipivalylethylene. It was concluded that a singlet oxygen was involved in the process which formed by a triplet-triplet annihilation at the interaction of 3O2 with a triplet-excited initial quinone.

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Authors and Affiliations

  1. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Moscow, 119991, Russia

    V. B. Vol’eva, I. S. Belostotskaya, N. L. Komissarova, Z. A. Starikova & L. N. Kurkovskaya

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  1. V. B. Vol’eva
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  2. I. S. Belostotskaya
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  3. N. L. Komissarova
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  4. Z. A. Starikova
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  5. L. N. Kurkovskaya
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Correspondence to N. L. Komissarova.

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Original Russian Text © V.B. Vol’eva, I.S. Belostotskaya, N.L. Komissarova, Z.A. Starikova, L.N. Kurkovskaya, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 243–245.

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Vol’eva, V.B., Belostotskaya, I.S., Komissarova, N.L. et al. Photooxygenolysis of 3,6-di-tert-butyl-o-benzoquinone. Russ J Org Chem 42, 227–229 (2006). https://doi.org/10.1134/S1070428002120114

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  • DOI: https://doi.org/10.1134/S1070428002120114

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