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Volumn , Issue 3, 2003, Pages 578-586

Low temperature, high conversion, liquid-phase benzylic oxidation with dioxygen by metal/NHPI-catalyzed co-oxidation with benzaldehyde

Author keywords

Chromium; Cobalt; Nickel; Oxidation; Oxygen

Indexed keywords

BENZALDEHYDE; BENZENE; CARBAMAZEPINE; CHROMIUM; COBALT; HYDROPEROXIDE; METAL; NICKEL; OXCARBAZEPINE; OXYGEN; PHTHALIMIDE DERIVATIVE;

EID: 0037322840     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (12)

References (42)
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    • Ebner, J.1    Riley, D.2
  • 14
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    • 2 in the absence of additional metal catalyst or aldehyde co-substrate
    • See also ref 15-16
    • 2 in the absence of additional metal catalyst or aldehyde co-substrate: Y Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. lwahama, Y. Nishiyama, J Org. Chem. 1995, 60, 3934-3935. See also ref 15-16.
    • (1995) J. Org. Chem. , vol.60 , pp. 3934-3935
    • Ishii, Y.1    Nakayama, K.2    Takeno, M.3    Sakaguchi, S.4    Iwahama, T.5    Nishiyama, Y.6
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    • note
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    • note
    • [7]
  • 19
    • 0034613165 scopus 로고    scopus 로고
    • Benzoic acid, formed from benzaldehyde during the co-oxidation, has recently been found to enhance the Co/NHPI-catalyzed alcohol oxidation
    • Benzoic acid, formed from benzaldehyde during the co-oxidation, has recently been found to enhance the Co/NHPI-catalyzed alcohol oxidation: T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J Org. Chem. 2000, 65, 6502-6507.
    • (2000) J. Org. Chem. , vol.65 , pp. 6502-6507
    • Iwahama, T.1    Yoshino, Y.2    Keitoku, T.3    Sakaguchi, S.4    Ishii, Y.5
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    • note
    • [6]).
  • 21
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    • note
    • The radical chain character of the reaction is also proven by the fact that no oxidation was observed in the presence of a trace amount of 2,6-di-tert-butyl-4-methylphenol as radical inhibitor.
  • 24
    • 0001379685 scopus 로고
    • The rate of oxidation of an unreactive substrate increases upon addition of a co-substrate that is readily oxidized provided that the rate of termination does not increase on addition of the cosubstrate
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    • 0013200673 scopus 로고    scopus 로고
    • note
    • In accordance with Ishii's observation (ref. 11), phthalimide has been detected as a decomposition product of NHPI. Gradual decomposition of NHPI to inert phthalimide accounts for the high amount of NHPI that is required in NHPI-catalyzed oxidations.
  • 27
    • 0013201529 scopus 로고    scopus 로고
    • [25] p. 40
    • [25] p. 40.
  • 28
    • 0013306188 scopus 로고    scopus 로고
    • note
    • 2. This could well be the mechanism behind initiation by cobalt, although Co concentrations under Ishii conditions are much larger than under our co-oxidation conditions.
  • 30
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    • [2], p. 245
    • [2], p. 245.
  • 35
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    • note
    • IV is also likely to be induced by perbenzoic acid.
  • 37
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    • (Eds.: J. C. Bailar, A. F. Trotman-Dickenson), Pergamon Press: Oxford
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    • (1973) Comprehensive Inorganic Chemistry
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  • 42
    • 0013200158 scopus 로고    scopus 로고
    • note
    • To prevent crystallization of benzoic acid in the PhCH supply tube. 10 vol% AcOH was added to the PhCH(O)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.