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Volumn 68, Issue 12, 2003, Pages 4999-5001

Trichloroisocyanuric/TEMPO oxidation of alcohols under mild conditions: A close investigation

Author keywords

[No Author keywords available]

Indexed keywords

PRIMARY ALCOHOLS;

EID: 0037940081     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034276b     Document Type: Article
Times cited : (160)

References (45)
  • 2
    • 0003678023 scopus 로고
    • ACS Monograph 186; American Chemical Society: Washington D.C.
    • (b) Hudlicky, M. Oxidation in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990.
    • (1990) Oxidation in Organic Chemistry
    • Hudlicky, M.1
  • 31
    • 0038744063 scopus 로고    scopus 로고
    • note
    • Using 1 equiv of TCCA the reaction is very slow and requires longer reaction time for completion.
  • 32
    • 0038405964 scopus 로고    scopus 로고
    • note
    • The presence of sodium or lithium halide is essential for the oxidation process, with no reaction taking place without it. NaBr is preferred owing to its higher solubility in acetone.
  • 37
    • 0038744060 scopus 로고    scopus 로고
    • note
    • From the stereochemistry of the recovered compounds it can be deduced that the chlorination of the double bond might arise from addition of chlorine, formed by oxidation of chloride ions, present in the solution, owing to the long reaction times.
  • 38
    • 0037729986 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis. In the absence of catalytic TEMPO, no reaction occurs.
  • 39
    • 0038744056 scopus 로고    scopus 로고
    • note
    • The hydrolysis of TCCA seems to be catalyzed by the presence of even catalytic amounts of halide ions; in the absence of traces of sodium halides, no oxidation to carboxylic acids takes place.
  • 40
    • 0038744061 scopus 로고    scopus 로고
    • note
    • It is noteworthy that bleach is not able to oxidize both 4-methoxybenzaldehyde and 4-methoxyphenyl acetaldeyde to the corresponding carboxylic acid, thus confirming the hypothesis that hypochlorous acid is formed in this step. In addition, TCCA is inactive in the absence of water.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.