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

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

Selective functionalizations of dimethyl 4-cyclohexene-l,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-H20-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 Me0H-H2S04-(C) system.

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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Efficient Conversion of Olefins into Epoxides, Bromohydrins, and Dibromides with Sodium Bromide in Water-Organic Solvent Electrolysis Systems'. Together they form a unique fingerprint.

Cite this