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 language | English |
|---|---|
| Pages (from-to) | 859-867 |
| Number of pages | 9 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 54 |
| Issue number | 10 |
| Publication status | Published - Oct 1996 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Electroorganic reactions mediated by vitamin B12 model complexes. / Hisaeda, Yoshio.
In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 54, No. 10, 10.1996, p. 859-867.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Electroorganic reactions mediated by vitamin B12 model complexes
AU - Hisaeda, Yoshio
PY - 1996/10
Y1 - 1996/10
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=0030261773&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0030261773
VL - 54
SP - 859
EP - 867
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 10
ER -