메뉴 건너뛰기




Volumn 75, Issue 3, 2010, Pages 733-740

Kinetic evidence for dihapto (η2) π-aryl participation in acid-catalyzed ring opening of diarylhomobenzoquinone epoxides

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBONDING ORBITAL; ARYL GROUP; CHEMICAL EQUATIONS; CYCLOBUTENE; ELECTRON DONATION; ELECTRON-DONATING ABILITY; GEOMETRICAL CHARACTERISTICS; KINETIC EVIDENCE; LINEAR FREE ENERGY RELATIONSHIPS; RING OPENING; RING OPENING REACTION; SUBSTITUENT EFFECT; TOPOLOGICAL FEATURES;

EID: 75749123873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902179x     Document Type: Article
Times cited : (7)

References (58)
  • 1
    • 75749130028 scopus 로고    scopus 로고
    • Lancelot, C. J.; Cram, D. J.; Scheyer, P. v. R. Carbenium Ions; Olah, G. A., Scheyer, P. v. R., Eds.;Wiley-Interscience: NewYork, 1972;3, Chapter 27, pp 1347-1483.
    • (a) Lancelot, C. J.; Cram, D. J.; Scheyer, P. v. R. Carbenium Ions; Olah, G. A., Scheyer, P. v. R., Eds.;Wiley-Interscience: NewYork, 1972;Vol. 3, Chapter 27, pp 1347-1483.
  • 8
    • 75749144027 scopus 로고    scopus 로고
    • Isaacs, N. S. Physical Organic Chemistry; Longman Science & Technical: Essex, 1995; Chapter 13, pp 643-700.
    • Isaacs, N. S. Physical Organic Chemistry; Longman Science & Technical: Essex, 1995; Chapter 13, pp 643-700.
  • 28
    • 75749137470 scopus 로고    scopus 로고
    • Crystallographic data for this compound have been deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via, by emailing data-request@ccdc. cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K, fax: +441223336033. CCDC 749514
    • Crystallographic data for this compound have been deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif, by emailing data-request@ccdc. cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +441223336033. CCDC 749514.
  • 29
    • 75749122001 scopus 로고    scopus 로고
    • Our attempt to follow the rate of the reaction of di(p-anisyl, homobenzoquinone epoxide by NMR failed because of the very fast degradation. Interestingly, this reaction gave neither 2- nor 3-type product but yielded di(anisyl)methyl-substituted benzoquinone derivative 6, which seems to arise from the cyclopropane ring cleavage as well as the loss of oxygen atom. The structure of 6 was determined by the X-ray crystal structural analysis see Supporting Information, CCDC 750112
    • Our attempt to follow the rate of the reaction of di(p-anisyl)- homobenzoquinone epoxide by NMR failed because of the very fast degradation. Interestingly, this reaction gave neither 2- nor 3-type product but yielded di(anisyl)methyl-substituted benzoquinone derivative 6, which seems to arise from the cyclopropane ring cleavage as well as the loss of oxygen atom. The structure of 6 was determined by the X-ray crystal structural analysis (see Supporting Information). CCDC 750112.
  • 31
    • 75749123223 scopus 로고    scopus 로고
    • 2 = 0.82, n = 8).
    • 2 = 0.82, n = 8).
  • 33
    • 0002585928 scopus 로고
    • Chapman, N. B, Shorter, J, Eds, Plenum Press: New York, Chapter 4, pp
    • (b) Shorter, J. Correlation Analysis in Chemistry. Recent Advances; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978; Chapter 4, pp 119-173.
    • (1978) Correlation Analysis in Chemistry. Recent Advances , pp. 119-173
    • Shorter, J.1
  • 38
    • 0001312924 scopus 로고
    • Trost, B. M, Ed, Pergamon Press: Oxford, U.K
    • (b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, pp 733-771.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733-771
    • Rickborn, B.1
  • 41
    • 33845948228 scopus 로고    scopus 로고
    • Richard, J. P. Ed, Elsevier Academic Press: London
    • (e) Whalen, D. E. Advances in Physical Organic Chemistry; Richard, J. P. Ed.; Elsevier Academic Press: London, 2005; Vol. 40, pp 247-298.
    • (2005) Advances in Physical Organic Chemistry , vol.40 , pp. 247-298
    • Whalen, D.E.1
  • 56
    • 35549012891 scopus 로고    scopus 로고
    • Recently, Wang and Tantillo suggested a stepwise reaction pathway for the acid-catalyzed transannular cyclization of 4 based on DFT calculations: Wang, S. C.; Tantillo, D. J. J. Org. Chem. 2007, 72, 8394-8401. However, the poor kinetic solvent effects for the reaction of 4 and especially for the present 1 explicitly rule out the intervention of the carbocation intermediate derived from the stepwise SN1 mechanism.
    • Recently, Wang and Tantillo suggested a stepwise reaction pathway for the acid-catalyzed transannular cyclization of 4 based on DFT calculations: Wang, S. C.; Tantillo, D. J. J. Org. Chem. 2007, 72, 8394-8401. However, the poor kinetic solvent effects for the reaction of 4 and especially for the present 1 explicitly rule out the intervention of the carbocation intermediate derived from the stepwise SN1 mechanism.
  • 57
    • 0001414996 scopus 로고    scopus 로고
    • Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y. H.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W. M.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van, Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C. P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J. Comput. Chem. 2000, 21, 1532-1548.
    • Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y. H.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W. M.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van, Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C. P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J. Comput. Chem. 2000, 21, 1532-1548.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.