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Volumn 2, Issue 19, 2000, Pages 2923-2926

Unprecedented direct oxygen atom transfer from hypervalent oxido-λ3-iodanes to α,β-unsaturated carbonyl compounds: Synthesis of α,β-epoxy carbonyl compounds

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EID: 0001127136     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006129v     Document Type: Article
Times cited : (37)

References (35)
  • 20
    • 0001557651 scopus 로고
    • Oxidation of tetracyanoethylene with iodosylbenzene affords tetracyanoethylene oxide. This reaction probably involves a nucleophilic attack of the oxygen atom of iodosylbenzene to the electron-deficient olefin. See: Moriarty, R. M.; Gupta, S. C.; Hu, H.; Berenschot, D. R.; White, K. B. J. Am. Chem. Soc. 1981, 103, 686.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 686
    • Moriarty, R.M.1    Gupta, S.C.2    Hu, H.3    Berenschot, D.R.4    White, K.B.5
  • 23
    • 0001961122 scopus 로고
    • Reaction of (diacetoxyiodo)benzene with hydroxide anion produces iodosylbenzene. See: Saltzman, H.; Sharefkin, J. G. Org. Synth. 1963, 43, 60.
    • (1963) Org. Synth. , vol.43 , pp. 60
    • Saltzman, H.1    Sharefkin, J.G.2
  • 24
    • 0042483547 scopus 로고    scopus 로고
    • note
    • 3: C, 54.65; H, 7.98; N, 2.77. Found: C, 54.26; H, 7.95; N, 2.75.
  • 25
    • 37049047413 scopus 로고
    • For syntheses of sodium, calcium, and ammonium 2-iodosylbenzoates, which show low solubility toward common organic solvents, see: (a) Baker, G. P.; Mann, F. G.; Sheppard, N.; Tetlow, A. J. J. Chem. Soc. 1965, 3721.
    • (1965) J. Chem. Soc. , pp. 3721
    • Baker, G.P.1    Mann, F.G.2    Sheppard, N.3    Tetlow, A.J.4
  • 30
    • 0042984340 scopus 로고    scopus 로고
    • note
    • The recovered diketone 3a in this epoxidation always consists of a mixture of (E)-and (Z)-isomers.
  • 35
    • 85088005600 scopus 로고    scopus 로고
    • note
    • 3-phenyliodanyl group shows a very high leaving group ability and is called a hyperleaving group. See ref 1o.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.