DOI: 10.1246/bcsj.67.847. Electrocatalytic Epoxidation of Cyclohexene by Manganese(III) Porphyrin Using Electron Mediator

Electrocatalytic Epoxidation of Cyclohexene by Manganese(III) Porphyrin Using Electron Mediator

10.1246/bcsj.67.847

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract For an electrocatalytic oxidation of cyclohexene in an air-equilibrated acetonitrile solution containing (5,10,15,20-tetraphenylporphyrinato)manganese(III) as a catalyst, benzoic anhydride as an acylating reagent and 1-methylimidazole as a ligand to Mn porphyrin, the addition of the compounds such as Methylene Blue, Safranine-T, and viologens promotes the production of cyclohexene oxide. The result implies that these compounds act effectively as mediators for the electron transfer from electrode to Mn porphyrin because they have more negative reduction potential than Mn porphyrin. The faradaic efficiency reaches about 100% by the use of benzylviologen under an optimum condition. But, in the presence of methylene blue, the maximum faradaic efficiency gives low values of about 30%. On the other hand, cyclohexene oxide is also produced by the use of zinc powder as a reductant, but the utilization efficiency of zinc gives relatively low values of 30—40% regardless of the kind of the mediator. This result is ascribed to the irreversible reduction of the mediator and the direct reaction of oxomanganese complex, which is an intermediate in this epoxidation reaction, with zinc powder.

Bibliography

Suzuki, Y., Koseki, Y., Takahashi, K., Matsui, S., & Komura, T. (1994). Electrocatalytic Epoxidation of Cyclohexene by Manganese(III) Porphyrin Using Electron Mediator. Bulletin of the Chemical Society of Japan, 67(3), 847â853.

Authors 5

Yoshihiro Suzuki (first)
Yoshiyuki Koseki (additional)
Kohshin Takahashi (additional)
Syuichi Matsui (additional)
Teruhisa Komura (additional)

References 13 Referenced 11

10.1021/ja00498a040
10.1021/ja00515a063
10.1021/ja00334a035
{'key': '2024011923444961600_r4'}
10.1021/ja00351a068
10.1021/ja00301a016
{'key': '2024011923444961600_r7'}
10.1021/ja00274a063
10.1016/0022-0728(88)80204-3
10.1246/bcsj.63.1374
{'key': '2024011923444961600_r11'}
{'key': '2024011923444961600_r12'}
{'key': '2024011923444961600_r13'}

Dates

Type	When
Created	19 years, 1 month ago (July 12, 2006, 1:35 a.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 6:44 p.m.)
Indexed	4 weeks, 2 days ago (Aug. 5, 2025, 8:54 a.m.)
Issued	31 years, 6 months ago (March 1, 1994)
Published	31 years, 6 months ago (March 1, 1994)
Published Online	19 years, 1 month ago (July 12, 2006)
Published Print	31 years, 6 months ago (March 1, 1994)

Funders 0

None

BibTeX

@article{Suzuki_1994, title={Electrocatalytic Epoxidation of Cyclohexene by Manganese(III) Porphyrin Using Electron Mediator}, volume={67}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.67.847}, DOI={10.1246/bcsj.67.847}, number={3}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Suzuki, Yoshihiro and Koseki, Yoshiyuki and Takahashi, Kohshin and Matsui, Syuichi and Komura, Teruhisa}, year={1994}, month=mar, pages={847–853} }

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