Electroorganic reactions mediated by vitamin B12 model complexes

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Abstract

It is shown that vitamin B12-dependent enzymes; involving the cobalt atoms as a catalytic center, mediate various isomerization reactions accompanied by carbon skeleton rearrangements. The rearrangements were investigated using the hydrophobic vitamin B12 derivatives under electrochemical conditions. As shown, the electrochemical carbon-skeleton rearrangements proceed via formation of anionic intermediates during the electrolysis of alkyl halides with various electron-seeking groups. The data suggest that the migration of a phenyl group on the β-carbon atom results in the formation of a radical intermediate. The enantiomer type is shown to be dependent on the hydrophobic vitamin B12 nature.

Original languageEnglish
Pages (from-to)859-867
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume54
Issue number10
Publication statusPublished - Oct 1996

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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