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Volumn , Issue 1, 2004, Pages 114-122

Novel model sulfur compounds as mechanistic probes for enzymatic and biomimetic oxidations

Author keywords

Electron transfer; Enzyme catalysis; Sulfide radical cation; Sulfoxidation

Indexed keywords

ALDEHYDE; ALKYL GROUP; AMMONIUM NITRATE; BENZOPHENONE; CATION; CERIUM; CERIUM AMMONIUM NITRATE; CHLORIDE PEROXIDASE; COPRINUS CINEREUS PEROXIDASE; HORSERADISH PEROXIDASE; HYDROPEROXIDE; PEROXIDASE; RADICAL; SOLVENT; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

EID: 11844255749     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400382     Document Type: Article
Times cited : (36)

References (69)
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    • Benzhydryl alcohol was stable in the presence of CAN, which allowed us to disregard its oxidation as a source of the benzophenone. Deprotonation of the radical cation is possible, even though in the absence of an additional base, due to the greater acidity of the benzhydryl hydrogen than the methylene hydrogen in the cinnamyl derivative. For literature regarding the α-deprotonation of the sulfide radical cation see: E. Baciocchi, C. Rol, E. Scamosci, G. V. Sebastiani, J. Org. Chem. 1991, 56, 5498-5502.
    • (1991) J. Org. Chem. , vol.56 , pp. 5498-5502
    • Baciocchi, E.1    Rol, C.2    Scamosci, E.3    Sebastiani, G.V.4
  • 21
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    • unpublished results
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    • Argüello, J.E.1
  • 22
    • 0003816493 scopus 로고
    • Plenum, New York
    • CAN is an extremely effective reagent for oxidative cleavage of vicinal diols, to afford the corresponding ketone or aldehyde derivatives. T. L. Ho, Organic Synthesis by Oxidation with Metal Compounds, Plenum, New York, 1986.
    • (1986) Organic Synthesis by Oxidation with Metal Compounds
    • Ho, T.L.1
  • 28
    • 11844261281 scopus 로고    scopus 로고
    • note
    • There are two sources of benzaldehyde (6): namely a) C-C bond fragmentation of the double bonds of the sulfides 4 and 5, and b) further oxidation of the cinnamyl alcohol primary product (8) (Scheme 3).
  • 31
    • 0000477130 scopus 로고    scopus 로고
    • -1: M. Ioele, S. Steenken, E. Baciocchi, J. Phys. Chem. A 1997, 101, 2979-2987. From our results in the photochemical oxidation with tetranitromethane, higher rate constants should be expected for the C-S fragmentation for sulfides 1c, 1d, 2 and 5.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 2979-2987
    • Ioele, M.1    Steenken, S.2    Baciocchi, E.3
  • 34
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    • note
    • IIICl has been reported. [21e]
  • 38
    • 11844278867 scopus 로고    scopus 로고
    • note
    • 2 in the absence of the (porphyrin)iron is also catalysed by the acid, making this reaction probe of little value.
  • 39
    • 2442502432 scopus 로고    scopus 로고
    • During the submission of this manuscript, an article about the chemoselectivity of the sulfoxidation reactions catalysed by [tetrakis(pentafluorophenyl)porphyrin]iron appeared: E. Baciocchi, M. F. Gerini, A. Lapi, J. Org. Chem. 2004, 69, 3586-3589.
    • (2004) J. Org. Chem. , vol.69 , pp. 3586-3589
    • Baciocchi, E.1    Gerini, M.F.2    Lapi, A.3
  • 42
    • 11844261280 scopus 로고    scopus 로고
    • note
    • Sulfide 2 was insoluble in the aqueous solution. In contrast, a homogeneous solution was formed when acetonitrile was added as a co-solvent.
  • 49
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    • (1991) Peroxidases in Chemistry and Biology , vol.2 , pp. 123-126
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.