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Volumn 7, Issue 1, 2001, Pages 297-302

Mild and efficient flavin-catalyzed H2O2 oxidations

Author keywords

Catalysis; Flavins; Homogeneous; Hydrogen peroxide; Oxidation

Indexed keywords

AMINE; FLAVINE MONONUCLEOTIDE; HYDROGEN PEROXIDE; QUERCETIN; THIOESTER;

EID: 0035808358     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010105)7:1<297::AID-CHEM297>3.0.CO;2-6     Document Type: Article
Times cited : (76)

References (47)
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    • (Ed.: D. N. Jones), Pergamon, Oxford, Sections 11.6 and 11.7
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    • (1979) Comprehensive Organic Chemistry , vol.5
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    • (Ed.: B. M. Trost), Pergamon, Oxford, Section 1.5
    • c) G. Solladie in Comprehensive Organic Synthesis, Vol. 6 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, Section 1.5;
    • (1991) Comprehensive Organic Synthesis , vol.6
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    • (Ed.: B. M. Trost), Pergamon, Oxford, Section 6.2.
    • d) S. Uemura in Comprehensive Organic Synthesis, Vol. 6 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, Section 6.2.
    • (1991) Comprehensive Organic Synthesis , vol.6
    • Uemura, S.1
  • 16
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    • For some examples where extreme or less economical conditions seem necessary see: a) S. Vayssié, H. Elias, Angew. Chem. 1998, 110, 2246; Angew. Chem. Int. Ed. 1998, 37, 2088 (use of in situ nitrous acid);
    • (1998) Angew. Chem. , vol.110 , pp. 2246
    • Vayssié, S.1    Elias, H.2
  • 17
    • 0032541273 scopus 로고    scopus 로고
    • use of in situ nitrous acid
    • For some examples where extreme or less economical conditions seem necessary see: a) S. Vayssié, H. Elias, Angew. Chem. 1998, 110, 2246; Angew. Chem. Int. Ed. 1998, 37, 2088 (use of in situ nitrous acid);
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2088
  • 24
    • 85007632107 scopus 로고    scopus 로고
    • note
    • The excess was mainly used to obtain better accuracy in the determination of the initial rate of the noncatalyzed reaction.
  • 25
    • 85007653134 scopus 로고    scopus 로고
    • note
    • Furthermore, simple alkenes such as styrene did not oxidize under the reaction conditions.
  • 27
    • 85007628816 scopus 로고    scopus 로고
    • note
    • Only partial decomposition of starting material (2-(phenylthio)-1,4-benzoquinone) could be detected by NMR.
  • 31
    • 85007628843 scopus 로고    scopus 로고
    • note
    • The oxidation of thioethers can be looked upon as a borderline case, since for example the equilibrium between I, IV, and III can play a greater role depending on experimental conditions.
  • 32
    • 85007643612 scopus 로고    scopus 로고
    • note
    • An alternative activation mechanism, even though less likely, where hydrogen peroxide electrophilically (!) attacks the flavin, can not be ruled out.
  • 33
    • 85007646622 scopus 로고    scopus 로고
    • note
    • Murahashi and co-workers have previously discussed such possible equilibria, see ref. [2].
  • 34
    • 85007643613 scopus 로고    scopus 로고
    • note
    • Murahashi used the perchlorate analogue of IVb as catalyst precursor.
  • 37
    • 85007646620 scopus 로고    scopus 로고
    • note
    • Fro example, the solubility and yields are rather low for most precursors substituted at positions 7, 8, and/or 10.
  • 40
    • 85007625392 scopus 로고    scopus 로고
    • note
    • The exact value was not determinable, since the melting point exceeded the max. temperature of the apparatus.
  • 41
    • 85007643104 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum.
  • 42
    • 85007643102 scopus 로고    scopus 로고
    • note
    • When using less catalyst/peroxide the reactions were followed up to 360 min with 30-60 min intervals after the first hour.
  • 44
    • 85007626314 scopus 로고    scopus 로고
    • note
    • When using less catalyst/peroxide the reactions were followed up to 360 min with 30-60 min intervals after the first hour.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.