Hydrophobic vitamin B12. Part 14. Ring-expansion reactions catalyzed by hydrophobic vitamin B12 under electrochemical conditions in nonaqueous medium

Yoshio Hisaeda, Junji Takenaka, Yukito Murakami

    Research output: Contribution to journalArticlepeer-review

    18 Citations (Scopus)

    Abstract

    The electrolysis of alicyclic ketones (5, 6, 7, and 8-membered rings) with a carboxylic ester and a bromomethyl group was carried out in N,N-dimethylformamide in the presence of a catalytic amount of heptamethyl cobyrinate perchlorate under various reaction conditions. The ring-expansion reaction largely proceeded at -2.0 V vs sce for all the substrates. The electrolysis plausibly proceeds as follows: the Co(II) complex as a catalyst is electrochemically reduced to the Co(I) species; the corresponding alkylated complex is generated by reaction of the supernucleophilic Co(I) species with an alicyclic bromide; the alkylated complex is subsequently decomposed by electrolysis to afford the final products; and the cobalt complex acts as a mediator repeatedly.

    Original languageEnglish
    Pages (from-to)2165-2172
    Number of pages8
    JournalElectrochimica Acta
    Volume42
    Issue number13-14
    DOIs
    Publication statusPublished - 1997

    All Science Journal Classification (ASJC) codes

    • Chemical Engineering(all)
    • Electrochemistry

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