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Volumn 37, Issue 11, 1981, Pages 2091-2096

Oxidation of α,β-un saturated aldehydes

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EID: 33748664603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)97963-3     Document Type: Article
Times cited : (1146)

References (30)
  • 1
    • 84918093048 scopus 로고    scopus 로고
    • B.S. Bal and H.W. Pinnick, submitted to J. Org. Chem.
  • 4
    • 0343416461 scopus 로고
    • In fact, primary allylic alcohols and benzylic alcohols give aldehydes when reacted with Jones reagent
    • (1975) J. Org. Chem. , vol.40 , pp. 1664
    • Harding1    May2    Dick3
  • 5
    • 33947086891 scopus 로고
    • Potassium permanganate oxidizes both aliphatic and aromatic aldehydes to acids but also will attack the double bond of α,β-unsaturated acids
    • (1973) J.Am.Chem.Soc. , vol.95 , pp. 3033
    • Lee1    Brownridge2
  • 6
    • 0001126182 scopus 로고
    • Potassium permanganate oxidizes both aliphatic and aromatic aldehydes to acids but also will attack the double bond of α,β-unsaturated acids
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3034
    • Wiberg1    Deutsch2    Rocek3
  • 9
    • 0000464825 scopus 로고
    • The mixture of silver oxide and base as in Marshall's paper and in, is necessary.
    • (1963) Org.Syn. , vol.4 Coll. , pp. 921
    • Campaigne1    Tullar2
  • 11
    • 84918093047 scopus 로고    scopus 로고
    • Cinnamaldehyde is oxidized to cinnamic acid by reaction with silver (II) oxide and sodium cyanide.
  • 20
    • 84918093046 scopus 로고    scopus 로고
    • Another hindered aldehyde (ii) can be oxidized to the corresponding methyl ester in 80% crude yield. This is the only example known to the authors of successful oxidation of a hindered aldehyde by this method. We thank Dr. Armand B. Pepperman for details of this conversion.
  • 22
    • 84918093045 scopus 로고    scopus 로고
    • The free alcohol 1 (RH) forms an unidentified compound when allowed to react With TMSCN.
  • 23
    • 84918093044 scopus 로고    scopus 로고
    • We thank Professor Wolfgang Kreiser for pointing out this method.
  • 24
    • 84918093043 scopus 로고    scopus 로고
    • 1H NMR, IR and GC/MS data.
  • 25
    • 84918093042 scopus 로고    scopus 로고
    • 1
  • 27
    • 33847086252 scopus 로고
    • Kraus has recently reported the use of 2-methyl-2-butene to take up the chlorine
    • (1980) J. Org. Chem. , vol.45 , pp. 1175
    • Kraus1    Taschner2
  • 28
    • 0001166068 scopus 로고
    • Kraus has recently reported the use of 2-methyl-2-butene to take up the chlorine
    • (1980) J.Org.Chem. , vol.45 , pp. 4825
    • Kraus1    Roth2
  • 29
    • 84918093041 scopus 로고    scopus 로고
    • The amounts of E and Z isomers were determined by GC analysis on a QF-1/carbowax column. The acids were analyzed as the methyl esters. We thank Dr. Richard R. Hautala for determining these ratios.
  • 30
    • 84918093040 scopus 로고    scopus 로고
    • We thank the Shell Chemical Company for a generous sample of “t-amylene”.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.