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Volumn 75, Issue 6, 2010, Pages 2115-2118

Computational study of factors controlling the boat and chair transition states of ireland-claisen rearrangements

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CLAISEN REARRANGEMENT; COMPUTATIONAL STUDIES; IRELAND; STERIC INTERACTIONS; TRANSITION STATE;

EID: 77949825560     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100033d     Document Type: Article
Times cited : (27)

References (38)
  • 3
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    • (c) Claisen, L. Chem. Ber. 1912, 45, 3157-3166.
    • (1912) Chem. Ber. , vol.45 , pp. 3157-3166
    • Claisen, L.1
  • 18
    • 64349087921 scopus 로고    scopus 로고
    • Recent related computational studies: (a)
    • Recent related computational studies: (a) Rehbein, J.; Leick, S.; Hiersemann, M. J. Org. Chem. 2009, 74, 1531-1540.
    • (2009) J. Org. Chem. , Issue.74 , pp. 1531-1540
    • Rehbein, J.1    Leick, S.2    Hiersemann, M.3
  • 21
    • 33845279007 scopus 로고
    • For reviews, see: (a) Ziegler, F. E.
    • For reviews, see: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
    • (1988) Chem. Rev. , vol.88 , pp. 1423-1452
  • 25
    • 84889453601 scopus 로고    scopus 로고
    • Hiersemann, M., Nubbemeyer, U., Eds.; Wiley-VCH: New York, Chapter 4
    • (e) McFarland, C. M.; McIntosh, M. C. In The Claisen Rearrangement; Hiersemann, M., Nubbemeyer, U., Eds.; Wiley-VCH: New York, 2007; Chapter 4, pp 117-210.
    • (2007) The Claisen Rearrangement , pp. 117-210
    • McFarland, C.M.1    McIntosh, M.C.2
  • 29
    • 0038626673 scopus 로고    scopus 로고
    • Revision D.01; Gaussian, Inc.: Wallingford, CT
    • Frisch, M. J. et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 30
    • 77949788978 scopus 로고    scopus 로고
    • Applying B3LYP/6-31+G(d) methodology, which was previously shown to be adequate, see: (a) Reference 12.
    • Applying B3LYP/6-31+G(d) methodology, which was previously shown to be adequate, see: (a) Reference 12.
  • 34
    • 77949861492 scopus 로고    scopus 로고
    • Conformational search was done at the AM1 level of theory, using SPARTAN; Wavefunction, Inc. All obtained conformers within a 5 kcal/ mol energy range were subsequently optimized with B3LYP/6-31+G(d) in Gaussian03.
    • Conformational search was done at the AM1 level of theory, using SPARTAN; Wavefunction, Inc. All obtained conformers within a 5 kcal/ mol energy range were subsequently optimized with B3LYP/6-31+G(d) in Gaussian03.
  • 35
    • 77949821556 scopus 로고    scopus 로고
    • Figures created with: CYLview, 1.0b; Legault, C. Y., Université de Sherbrooke, 2009 (http://www.cylview.org).
    • Figures created with: CYLview, 1.0b; Legault, C. Y., Université de Sherbrooke, 2009 (http://www.cylview.org).
  • 37
    • 77949860711 scopus 로고    scopus 로고
    • We calculated the silyl analogue of E'-6-boat-TS with OTMS instead of OMe. The activation barrier of the rearrangement is 25.8 kcal/mol and the free energy of reaction is -32.9 kcal/mol, indicating that the OMe model is adequate.
    • We calculated the silyl analogue of E'-6-boat-TS with OTMS instead of OMe. The activation barrier of the rearrangement is 25.8 kcal/mol and the free energy of reaction is -32.9 kcal/mol, indicating that the OMe model is adequate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.