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Volumn 125, Issue 48, 2003, Pages 14674-14675

First Direct Evidence for Stereospecific Olefin Epoxidation and Alkane Hydroxylation by an Oxoiron(IV) Porphyrin Complex

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE; PORPHYRIN DERIVATIVE;

EID: 0345293202     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0368204     Document Type: Article
Times cited : (141)

References (28)
  • 12
    • 0344113578 scopus 로고    scopus 로고
    • note
    • 2O concentration in the reaction solutions.
  • 13
    • 0344545196 scopus 로고    scopus 로고
    • note
    • The formation of an iron(III) porphyrin complex may be the result of a facile oxidation of an iron(II) porphyrin complex, a product formed upon the oxygen atom transfer from 2 to organic substrates, by another oxoiron(IV) porphyrin molecule: see ref 4.
  • 14
    • 0344976132 scopus 로고    scopus 로고
    • note
    • The observations that the reaction rates of 2 toward olefins depend on olefin substrates (Table 1) and the amounts of cyclohexene (Supporting Information, Figure S5) demonstrate that 2 is indeed involved in the olefin epoxidation reactions.
  • 22
    • 0344545197 scopus 로고    scopus 로고
    • note
    • 18O into oxygenated products was high at room temperature. These different reactivity patterns indicate that the hydroxylating intermediate generated in the reaction of 1 and m-CPBA under catalytic conditions at -40 °C is different from 2.
  • 23
    • 0344113577 scopus 로고    scopus 로고
    • note
    • IV=O complex disappeared immediately upon the addition of the substrate at -40 °C and yielded 55% of alcohol product, whereas 2 was stable in the presence of the substrate at -40 °C and yielded no alcohol product under the identical conditions.
  • 26
    • 0032584090 scopus 로고    scopus 로고
    • An iron(III)-hydroperoxide porphyrin complex has been suggested as a "second electrophilic oxidant" that effects olefin epoxidation and alkane hydroxylation in cytochromes P450: (a) Vaz, A. D. N.; McGinnity, D. F.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3555-3560.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 3555-3560
    • Vaz, A.D.N.1    McGinnity, D.F.2    Coon, M.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.