Efficient conversion of olefins into epoxides, bromohydrins, and dibromides with sodium bromide in water-organic solvent electrolysis systems

Sigeru Torii, Kenji Uneyama, Hideo Tanaka, Tooru Yamanaka, Tsuneo Yasuda, Michio Ono, Yumiko Kohmoto

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40 Citations (Scopus)

Abstract

Selective functionalizations of dimethyl 4-cyclohexene-1,2-dicarboxylate (1) and acyclic olefins 5 into the corresponding epoxides 2 and 6, bromohydrins 3 and 7, and 1,2-dibromides 4 and 8 were performed by electrolysis in a MeCN-H2O-NaBr-(Pt) system. Lower Br- concentration (less than 0.05 M) facilitates the formation of 2 in neutral medium and of 3 in acidic medium, whereas higher Br- concentration (more than 1.5 M in acidic medium) produced exclusively 4. The effective C-C bond cleavage of the epoxy group of 2, leading to the corresponding diacetal 10, was also accomplished by electrolysis in a MeOH-H2SO4-(C) system.

Original languageEnglish
Pages (from-to)3312-3315
Number of pages4
JournalJournal of Organic Chemistry
Volume46
Issue number16
Publication statusPublished - 1981

ASJC Scopus subject areas

  • Organic Chemistry

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    Torii, S., Uneyama, K., Tanaka, H., Yamanaka, T., Yasuda, T., Ono, M., & Kohmoto, Y. (1981). Efficient conversion of olefins into epoxides, bromohydrins, and dibromides with sodium bromide in water-organic solvent electrolysis systems. Journal of Organic Chemistry, 46(16), 3312-3315.