메뉴 건너뛰기




Volumn 9, Issue 23, 2007, Pages 4873-4876

Ab initio and density functional theory evidence on the rate-limiting step in the Morita-Baylis-Hillman reaction

Author keywords

[No Author keywords available]

Indexed keywords


EID: 36349022163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702211d     Document Type: Article
Times cited : (79)

References (40)
  • 3
  • 4
    • 36348930025 scopus 로고    scopus 로고
    • Morita, K. Japan Patent 6803364, 1968; Chem. Abstr. 1968, 69, 58828s.
    • (d) Morita, K. Japan Patent 6803364, 1968; Chem. Abstr. 1968, 69, 58828s.
  • 21
    • 33747876396 scopus 로고    scopus 로고
    • 3-catalyzed MBH reaction between acrylonitrile and acetaldehyde. Xu, J. THEOCHEM 2006, 767, 61.
    • 3-catalyzed MBH reaction between acrylonitrile and acetaldehyde. Xu, J. THEOCHEM 2006, 767, 61.
  • 23
    • 36348939998 scopus 로고    scopus 로고
    • The CBS-4M is known to give highly accurate energies for organic reactions/systems,
    • (a) The CBS-4M is known to give highly accurate energies for organic reactions/systems,
  • 26
    • 0033731344 scopus 로고    scopus 로고
    • For the mPW1K method see: Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
    • (d) For the mPW1K method see: Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
  • 27
    • 36348990302 scopus 로고    scopus 로고
    • All calcuations have been carried out with Gaussian03 suite of quantum chemical programs. Frisch et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004 (see the Supporting Information for the full citation),
    • (e) All calcuations have been carried out with Gaussian03 suite of quantum chemical programs. Frisch et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004 (see the Supporting Information for the full citation),
  • 28
    • 36348978839 scopus 로고    scopus 로고
    • Intermediates and transition states are respectively charecterized as minima and first order saddle points, using frequency analysis. Authenticity of the transition states was verified both by normal modes analysis and by intrinsic reaction coordinate calculations
    • (f) Intermediates and transition states are respectively charecterized as minima and first order saddle points, using frequency analysis. Authenticity of the transition states was verified both by normal modes analysis and by intrinsic reaction coordinate calculations.
  • 29
    • 36348996099 scopus 로고    scopus 로고
    • See Table S1 in the Supporting Information for full details on the energies of various intermediates (na, nb, nc, nd, where n = 1 or 2) involved in the reaction.
    • See Table S1 in the Supporting Information for full details on the energies of various intermediates (na, nb, nc, nd, where n = 1 or 2) involved in the reaction.
  • 30
    • 36348976488 scopus 로고    scopus 로고
    • See the Supporting Information for further details on computational methods
    • See the Supporting Information for further details on computational methods.
  • 31
    • 0000482912 scopus 로고    scopus 로고
    • Similar situations involving four-membered TS were reported earlier. See: a
    • Similar situations involving four-membered TS were reported earlier. See: (a) Hall, N. E.; Smith, B. J. J. Phys. Chem. A 1998, 102, 4930.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 4930
    • Hall, N.E.1    Smith, B.J.2
  • 32
    • 35549012892 scopus 로고    scopus 로고
    • published online Sept 27
    • (b) Patil, M. P.; Sunoj, R. B. J. Org. Chem., published online Sept 27, http:/ dxdoi.org/10.1021/jo071004q.
    • J. Org. Chem
    • Patil, M.P.1    Sunoj, R.B.2
  • 37
    • 36348963734 scopus 로고    scopus 로고
    • See Table S2 and Figure S3 in the Supporting Information.
    • See Table S2 and Figure S3 in the Supporting Information.
  • 38
    • 0027462799 scopus 로고    scopus 로고
    • The Michael acceptor should bear a good leaving group attached to the carbonyl to be able to form a cylic dioxanone. See: (a) Drewes, S. E, Emslie, N. D, Field, J. S, Khan, A. A, Ramesar, N. S. Tetrahedron Lett. 1993, 34, 1205
    • The Michael acceptor should bear a good leaving group attached to the carbonyl to be able to form a cylic dioxanone. See: (a) Drewes, S. E.; Emslie, N. D.; Field, J. S.; Khan, A. A.; Ramesar, N. S. Tetrahedron Lett. 1993, 34, 1205.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.