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Volumn 65, Issue 6, 2000, Pages 1818-1824

Benzocyclobutene: The impact of fusing a strained ring onto benzene

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CYCLOBUTANE DERIVATIVE;

EID: 0034708731     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991825y     Document Type: Article
Times cited : (16)

References (60)
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    • (a) For a recent review see: Maksic, Z. B.; Eckert-Maksic, M.; Mó, O.; Yañez, M. In Pauling's Legacy: Modern Modelling of the Chemical Bond; Maksic, Z. B., Orville-Thomas, W. J., Eds. Theoretical and Computational Chemistry; Politzer, P., Maksic, Z. B., Eds.; Elsevier: Amsterdam, 1999; Vol. 3, and references therein.
    • (1999) Theoretical and Computational Chemistry , vol.3
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  • 3
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    • Chemistry of Cycloproparenes
    • Thummel, R. P., Ed.; JAI Press: Greenwich, CT
    • (c) Muller, P. Chemistry of Cycloproparenes. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 3, pp 37-107.
    • (1995) Advances in Theoretically Interesting Molecules , vol.3 , pp. 37-107
    • Muller, P.1
  • 14
    • 0000764545 scopus 로고
    • The procedure described in ref 11 was followed with the exception that the reaction mixture was refluxed in decalin for 18 h. The reaction was carried out in an apparatus similar to that described in Hudecek, M.; Toma, S. J. Organomet. Chem. 1990, 393, 115-118.
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    • Hudecek, M.1    Toma, S.2
  • 20
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    • 7-Chlorobenzocyclobutene was prepared by reduction and subsequent chlorination of benzocyclobutenone as described by Azadi-Ardakani, M.; Wallace, T. W. Tetrahedron 1988, 44, 5939-5952.
    • (1988) Tetrahedron , vol.44 , pp. 5939-5952
    • Azadi-Ardakani, M.1    Wallace, T.W.2
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    • Maksic, Z. B., Ed.; Springer-Verlag: Berlin-Heidelberg
    • (a) Maksic, Z. B. In Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer-Verlag: Berlin-Heidelberg, 1991; Vol. 2, p 137.
    • (1991) Theoretical Models of Chemical Bonding , vol.2 , pp. 137
    • Maksic, Z.B.1
  • 42
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    • (b) The implementation in Gaussian 94 is due to Cioslowski and co-workers. See: Cioslowski, J.; Nanayakkara, A.; Challacombe, M. Chem. Phys. Lett. 1993, 203, 137-142 and the Gaussian 94 manual for more details.
    • (1993) Chem. Phys. Lett. , vol.203 , pp. 137-142
    • Cioslowski, J.1    Nanayakkara, A.2    Challacombe, M.3
  • 47
    • 0343850991 scopus 로고    scopus 로고
    • The B3LYP data are available in the Supporting Information
    • The B3LYP data are available in the Supporting Information.
  • 48
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    • The acidity of certain positions can be estimated from the corresponding s-character according to the following relationship: pK = 83.12 - 1.33(%s). (a) Maksic, Z. B.; Eckert-Maksic, M. Tetrahedron 1969, 25, 5113-5126. (b) Merill, G. N.; Kass, S. R. J. Phys. Chem. 1996, 100, 17465-17471.
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  • 49
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    • The acidity of certain positions can be estimated from the corresponding s-character according to the following relationship: pK = 83.12 - 1.33(%s). (a) Maksic, Z. B.; Eckert-Maksic, M. Tetrahedron 1969, 25, 5113-5126. (b) Merill, G. N.; Kass, S. R. J. Phys. Chem. 1996, 100, 17465-17471.
    • (1996) J. Phys. Chem. , vol.100 , pp. 17465-17471
    • Merill, G.N.1    Kass, S.R.2
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    • note
    • 13C-H + 455.3, which is taken from ref 33.
  • 55
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    • MP2 calculations were not carried out because they typically give poor results for electron affinities, whereas B3LYP values are usually quite good. For example, see Merrill, G. N.; Kass S. R. J. Am. Chem. Soc. 1997, 119, 12322-12337.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12322-12337
    • Merrill, G.N.1    Kass, S.R.2
  • 60
    • 0342545352 scopus 로고    scopus 로고
    • note
    • For consistency sake, we have used the same numbering scheme for 1 as for 1H, 1α, and 1β. As a result, C8 is the anionic carbon in 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.