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Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide

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Abstract

Optimal conditions were found for induced hydroxyhalogenation of cyclic dienes (tetrahydroindene, 4-vinylcyclohexene and 5-vinyl- and 5-cyclohexenylbicyclo[2.2.1]hept-2-enes) in the system [MHlg-HA or HHlg]-H2O2 (or NaClO). Dehydrohalogenation of the chloro- and bromohydrins thus obtained with powdered potassium carbonate gave the corresponding diepoxy derivatives, and their hydrolysis led to mixtures of stereoisomeric tetrahydric alcohols.

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Authors and Affiliations

  1. Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, pr. Khodzhaly 30, Baku, AZ 1025, Azerbaijan

    Kh. M. Alimardanov, O. A. Sadygov, N. I. Garibov & M. Ya. Abdullaeva

Authors
  1. Kh. M. Alimardanov
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  2. O. A. Sadygov
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  3. N. I. Garibov
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  4. M. Ya. Abdullaeva
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Correspondence to O. A. Sadygov.

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Original Russian Text © Kh.M. Alimardanov, O.A. Sadygov, N.I. Garibov, M.Ya. Abdullaeva, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1307–1312.

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Alimardanov, K.M., Sadygov, O.A., Garibov, N.I. et al. Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide. Russ J Org Chem 48, 1302–1308 (2012). https://doi.org/10.1134/S1070428012100077

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  • DOI: https://doi.org/10.1134/S1070428012100077

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