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Volumn 13, Issue 7, 2011, Pages 1848-1851

Ring-enlargement reactions of donor-acceptor-substituted cyclopropanes: Which combinations are most efficient?

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EID: 79953203616     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200355f     Document Type: Article
Times cited : (89)

References (41)
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    • For reviews on donor-acceptor-substituted cyclopropanes and their reactivity
    • For reviews on donor-acceptor-substituted cyclopropanes and their reactivity: Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
    • (2003) Chem. Rev. , vol.103 , pp. 1151-1196
    • Reissig, H.-U.1    Zimmer, R.2
  • 24
    • 0039573069 scopus 로고    scopus 로고
    • A theoretical study has been performed for cyclopropane-carbaldehyde and for vinylcyclopropancarbaldehyde
    • A theoretical study has been performed for cyclopropane-carbaldehyde and for vinylcyclopropancarbaldehyde: Sperling, D.; Reissig, H.-U.; Fabian, J. Eur. J. Org. Chem. 1999, 1107-1114
    • (1999) Eur. J. Org. Chem. , pp. 1107-1114
    • Sperling, D.1    Reissig, H.-U.2    Fabian, J.3
  • 26
    • 0242407233 scopus 로고    scopus 로고
    • Retro-ene reactions of methyl substituted nitrosocyclopropanes are known
    • Retro-ene reactions of methyl substituted nitrosocyclopropanes are known: Yu, Z.-X.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 13825-13830
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13825-13830
    • Yu, Z.-X.1    Houk, K.N.2
  • 36
    • 0038626673 scopus 로고    scopus 로고
    • revision C.02; Gaussian, Inc.: Wallingford, CT, (see Supporting Information for the complete citation).
    • Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004, (see Supporting Information for the complete citation).
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 37
    • 0030668117 scopus 로고    scopus 로고
    • For representative examples we also used the unrestricted open-shell (U)DFT procedure in order to allow biradicaloid singlet transition states. However, biradicaloid singlet transition states were not observed. Corresponding triplet transition states were found to be higher in energy. Hence, a dipolar mechanism is assumed, which is in contrast to vinylcyclopropane/cyclopentene rearrangement
    • For representative examples we also used the unrestricted open-shell (U)DFT procedure in order to allow biradicaloid singlet transition states. However, biradicaloid singlet transition states were not observed. Corresponding triplet transition states were found to be higher in energy. Hence, a dipolar mechanism is assumed, which is in contrast to vinylcyclopropane/cyclopentene rearrangement: Houk, K. N.; Nendel, M.; Wiest, O.; Storer, J. W. J. Am. Chem. Soc. 1997, 119, 10545-10546
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10545-10546
    • Houk, K.N.1    Nendel, M.2    Wiest, O.3    Storer, J.W.4
  • 41
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    • For the evaluation of solvent effects the self-consistent reaction field (SCRF) theory using the PCM-united atom topological model (UAHF, radii of interlocking spheres) was employed as implemented in Gaussian 03
    • For the evaluation of solvent effects the self-consistent reaction field (SCRF) theory using the PCM-united atom topological model (UAHF, radii of interlocking spheres) was employed as implemented in Gaussian 03: Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
    • (2005) Chem. Rev. , vol.105 , pp. 2999-3093
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.