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Solid-phase bromination of hindered phenols

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Abstract

The solid-Phase bromination of a series oftert-butyl-substituted phenols withN-bromosuccinimide and dioxane dibromide afforded halogenated cyclohexadienones, quinobromides. Under the extrusion conditions, the latter underwent further transformations, mainly, debromination. A new reaction, dioxane dibromide catalyzed anhydroheterocyclization of 2,2′-dihydroxy-3,3′,5,5′-tetra-tert-butyldiphenyl to 2,4,6,8-tetra-tert-butyldibenzofuran, was discovered and the mechanism of this reaction was proposed.

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Authors and Affiliations

  1. N. M. Emanuel' Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 117977, Moscow, Russian Federation

    Y. B. Vol'eva, I. S. Belostotskaya, N. L. Komissarova & V. V. Ershov

Authors
  1. Y. B. Vol'eva
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  2. I. S. Belostotskaya
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  3. N. L. Komissarova
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  4. V. V. Ershov
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1310–1312, May, 1996.

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Vol'eva, Y.B., Belostotskaya, I.S., Komissarova, N.L. et al. Solid-phase bromination of hindered phenols. Russ Chem Bull 45, 1249–1251 (1996). https://doi.org/10.1007/BF01431636

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