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Volumn 68, Issue 4, 2003, Pages 1334-1338

Cyclization of aryllithiums tethered to methylenecycloalkanes: Stereoselective synthesis of 4α-substituted cis-hexahydrofluorenes

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 0037458868     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020593r     Document Type: Article
Times cited : (34)

References (26)
  • 5
    • 0001433726 scopus 로고
    • Mechanisms of importance in synthesis
    • Coxon, J. M., Ed.; JAI Press: Greenwich, CT
    • (a) Bailey, W. F.; Ovaska, T. V. Mechanisms of Importance in Synthesis. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273.
    • (1994) Advances in Detailed Reaction Mechanisms , vol.3 , pp. 251-273
    • Bailey, W.F.1    Ovaska, T.V.2
  • 19
    • 0001415863 scopus 로고    scopus 로고
    • By way of comparison, the half-time for cyclization of the parent 5-hexenyllithium in the presence of TMEDA is ∼6 min at -30 °C. See: Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361.
    • (1998) J. Org. Chem. , vol.63 , pp. 361
    • Bailey, W.F.1    Carson, M.W.2
  • 23
    • 0242497688 scopus 로고    scopus 로고
    • note
    • 7 it is necessary to conduct the lithium-bromine exchange in a solvent system that contains a dialkyl ether, it is not possible to prepare the aryllithium in good yield in a pure hydrocarbon solvent.
  • 24
    • 0000057455 scopus 로고
    • 6d Indeed, intramolecular coordination of the lithium atom with the remote π-bond in the ground state of 5-hexenyllithium has been experimentally confirmed; see: Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6577
    • Bailey, W.F.1    Punzalan, E.R.2
  • 25
    • 37049068007 scopus 로고
    • 6d Indeed, intramolecular coordination of the lithium atom with the remote π-bond in the ground state of 5-hexenyllithium has been experimentally confirmed; see: Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1953
    • Rölle, T.1    Hoffmann, R.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.