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Volumn 63, Issue 16, 1998, Pages 5617-5622

Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation

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EID: 0000775853     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980542n     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 85034481136 scopus 로고    scopus 로고
    • Osaka University
    • (a) Osaka University,
  • 2
    • 85034485940 scopus 로고    scopus 로고
    • Heriot-Watt University
    • (b) Heriot-Watt University.
  • 5
    • 0003391908 scopus 로고
    • (b) Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol. 1; 1982; Vol. 2.
    • (1982) Ozonation in Organic Chemistry , pp. 2
  • 10
    • 85034463004 scopus 로고    scopus 로고
    • 1H NMR (the chemical shifts and the ratio of the peak areas) and IR spectra (strong ozonide bands but only a weak aldehyde band), the oligomers 3a,b seem to have a normal ozonide structure: (a) ref 2a; Vol. 1, pp 33-37. (b) Murray, R. W.; Su, J.-S. J. Org. Chem. 1983, 48, 817.
    • Angew. Chem., Int. Ed. Engl. , vol.1 , pp. 33-37
  • 11
    • 0000624495 scopus 로고
    • 1H NMR (the chemical shifts and the ratio of the peak areas) and IR spectra (strong ozonide bands but only a weak aldehyde band), the oligomers 3a,b seem to have a normal ozonide structure: (a) ref 2a; Vol. 1, pp 33-37. (b) Murray, R. W.; Su, J.-S. J. Org. Chem. 1983, 48, 817.
    • (1983) J. Org. Chem. , vol.48 , pp. 817
    • Murray, R.W.1    Su, J.-S.2
  • 22
    • 0027969949 scopus 로고
    • Ozonolyses of the regioisomers of keto vinyl ethers; (a) Bunnelle, W. H.; Lee, S.-G. Tetrahedron Lett. 1994, 35, 8141. (b) McCullough, K. J.; Nakamura, N.; T. Fujisaka, T.; Nojima, M.; Kusabayashi, S. J. Am. Chem. Soc. 1991, 113, 1786.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8141
    • Bunnelle, W.H.1    Lee, S.-G.2
  • 25
    • 0029116270 scopus 로고
    • The increased formation of ozonide 2c in the reaction in the presence of trifluoroacetophenone (90%) as compared with the reaction in the absence of the additive (52%) would be interpreted as that this polar additive would stabilize the carbonyl oxide moiety by coordination, thereby suppressing the oligomerization quite significantly. A similar assistance by a polar nitrone in ozonide formation has been observed for the ozonolysis of acenaphthylene: Satake, S.; Ushigoe, Y.; Nojima, M.; McCullough, K. J. J. Chem. Soc., Chem. Commun. 1995, 1469.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 1469
    • Satake, S.1    Ushigoe, Y.2    Nojima, M.3    McCullough, K.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.