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Titolo:
DIOXYGEN-ACTIVATED REDUCTIVE EPOXIDATION OF CYCLOHEXENE USING MN(III)PORPHYRIN-VIOLOGEN CATALYTIC-SYSTEMS
Autore:
TSUDA Y; TAKAHASHI K; YAMAGUCHI T; MATSUI S; KOMURA T; NISHIGUCHI I;
Indirizzi:
FUKUI NATL COLL TECHNOL,DEPT BIOL & CHEM ENGN GESHI SABAE 9168507 JAPAN KANAZAWA UNIV,DEPT CHEM & CHEM ENGN,FAC ENGN KANAZAWA ISHIKAWA 920866JAPAN NAGAOKA UNIV TECHNOL,DEPT CHEM NAGAOKA NIIGATA 9402137 JAPAN
Titolo Testata:
Nippon kagaku kaishi
fascicolo: 9, , anno: 1998,
pagine: 581 - 590
SICI:
0369-4577(1998):9<581:DREOCU>2.0.ZU;2-3
Fonte:
ISI
Lingua:
JPN
Soggetto:
MANGANESE-PORPHYRINS; AXIAL LIGANDS; MODEL SYSTEM; METALLOPORPHYRINS; CYTOCHROME-P-450; HYDROCARBONS; OXIDATION; IMIDAZOLE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
22
Recensione:
Indirizzi per estratti:
Citazione:
Y. Tsuda et al., "DIOXYGEN-ACTIVATED REDUCTIVE EPOXIDATION OF CYCLOHEXENE USING MN(III)PORPHYRIN-VIOLOGEN CATALYTIC-SYSTEMS", Nippon kagaku kaishi, (9), 1998, pp. 581-590

Abstract

When a viologen-linked Mn(III) porphyrin complex as well as a mixed system of Mn(III) porphyrin and hexylviologen were used as a catalyst for a monooxygenation reaction of cyclohexene in an air-equilibrated dichloromethane suspension containing insoluble zinc powder as a reductant and benzoic anhydride as a cleaving reagent of dioxygen O-O bond, cyclohexene oxide(epoxide) was obtained as a single oxidation product of cyclohexene. Cyclic voltammetry was carried out to clarify the role of the molecular dioxygen, hexylviologen, l-methyl-imidazole (1-MeIm) and benzoic anhydride for the redox characteristics of the Mn porphyrin, and to explain this catalytic mechanism. It was consequently provedthat the coordination of 1-MeIm to Mn(III/II) porphyrins let to vary the redox potential of its couple and also the coordination of 1-MeIm to Mn(II) porphyrin interfered with that of the molecular dioxygen to its porphyrin, and hexylviologen acted as a mediator of electron transfer from zinc powder to Mn(ll) porphyrin-O-2 adduct. Therefore, the amount of the produced epoxide varied complexly with concentration of 1-MeIm added in this catalytic system. The larger amount of epoxide was obtained in the mixed system using the Mn porphyrin that has more positive redox potential, because the reduction of the Mn porphyrin occurred more easily.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 16:18:47