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Volumn 69, Issue 25, 2004, Pages 8676-8680

Remarkable substituent effects on the oxidizing ability of triarylbismuth dichlorides in alcohol oxidation

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BENZENE; CHEMICAL BONDS; ELECTRONS; MOLECULAR DYNAMICS; OXIDATION;

EID: 10044298571     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485740     Document Type: Article
Times cited : (23)

References (32)
  • 1
    • 0003816493 scopus 로고
    • Mijs, W. J., De Jonge, C. R. H. I., Eds.; Plenum: New York; Chapter 15
    • (a) Kitchin, J. P. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., De Jonge, C. R. H. I., Eds.; Plenum: New York, 1986; Chapter 15, pp 817-837.
    • (1986) Organic Synthesis by Oxidation with Metal Compounds , pp. 817-837
    • Kitchin, J.P.1
  • 4
    • 0003068639 scopus 로고    scopus 로고
    • Suzuki, H., Matano, Y., Eds.; Elsevier: New York, Chapter 5
    • (d) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y., Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440.
    • (2001) Organobismuth Chemistry , pp. 371-440
    • Komatsu, N.1
  • 16
    • 10044221618 scopus 로고    scopus 로고
    • note
    • 3Bi. Thus, the reported relative rate values are not used here for quantitative discussion.
  • 20
    • 10044260600 scopus 로고    scopus 로고
    • note
    • 2), 7.62 (d, 6H, J = 8.5 Hz, ArH), and 8.28 (d, 6H, J = 8.5 Hz, ArH). In the presence or absence of the alcohol, a 1·DBU type complex was also formed as an equilibrium mixture with 1 and DBU. Thus, the intermediate A may be formed via the complex 1·DBU.
  • 22
    • 10044262873 scopus 로고
    • Interscience: New York, and references therein
    • Molecular Rearrangements; de Mayo, P., Ed.; Interscience: New York, 1964; Vol. 1, p 22, and references therein.
    • (1964) Molecular Rearrangements , vol.1 , pp. 22
    • De Mayo, P.1
  • 23
    • 10044292637 scopus 로고    scopus 로고
    • note
    • Addition of excess 1,1-diphenylethene did not depress the yield of 4, ruling out the involvement of free radical species.
  • 24
    • 10044296875 scopus 로고    scopus 로고
    • note
    • If the first step consists of a slow equilibrium compared to the second step, it would become a rate-determining step. In such a case, however, a small secondary isotope effect should be observed for the intermolecular competition reactions.
  • 25
    • 0000877220 scopus 로고
    • In the Swern oxidation of PhCH(D)OH, the intramolecular H/D isotope effect of 2.6 ± 0.3 was observed. See: Marx, M.; Tidwell, T. T. J. Org. Chem. 1984, 49, 788.
    • (1984) J. Org. Chem. , vol.49 , pp. 788
    • Marx, M.1    Tidwell, T.T.2
  • 26
    • 10044278916 scopus 로고    scopus 로고
    • note
    • 3 derivative 1e due to the electronic repulsion between the o-trifluoromethyl substituents and the alkoxy oxygen atom.
  • 28
    • 33845183452 scopus 로고
    • Trifluoromethyl carbinols are known to resist oxidation and, at present, only a few methods are available for their conversion to the corresponding trifluoromethyl ketones. For example, see: (a) Linderman, R. J.; Graves, D. M. J. Org. Chem. 1989, 54, 661.
    • (1989) J. Org. Chem. , vol.54 , pp. 661
    • Linderman, R.J.1    Graves, D.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.