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Volumn , Issue 12, 1996, Pages 2007-2013

Rearrangement of donor-acceptor-substituted vinylcyclopropanes to functionalized cyclopentene derivatives: Evidence for zwitterionic intermediates

Author keywords

1,3 Zwitterions; Cyclopentenes; Rearrangement; Solvent effect; Vinylcyclopropanes, donor acceptor substituted

Indexed keywords


EID: 33748957523     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961210     Document Type: Article
Times cited : (17)

References (44)
  • 1
    • 33748973785 scopus 로고
    • Dissertation, Technische Hochschule Darmstadt
    • M. Buchert, Dissertation, Technische Hochschule Darmstadt, 1992.
    • (1992)
    • Buchert, M.1
  • 4
    • 0001373505 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, chapter 8.1
    • T. Hudlicky, J. W. Reed in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, vol. 5, chapter 8.1, p. 899-970.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899-970
    • Hudlicky, T.1    Reed, J.W.2
  • 7
    • 0000584447 scopus 로고
    • For theoretical studies concerning the vinylcyclopropane-cyclopentene rearrangement: K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739;
    • (1992) Angew. Chem. , vol.104 , pp. 711-739
    • Houk, K.N.1    Li, Y.2    Evanseck, J.D.3
  • 13
    • 0029132258 scopus 로고
    • For a one-electron oxidation catalyzed rearrangement see: J. P. Dinnocenzo, D. A. Coulon. Tetrahedron Lett. 1995, 36, 7415-7418, and references cited.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7415-7418
    • Dinnocenzo, J.P.1    Coulon, D.A.2
  • 27
    • 0006600971 scopus 로고
    • For the heteroanalogous system cyclopropanecarboxaldehyde is formed from 2,3-dihydrofuran at temperatures higher than 375°C; C. L. Wilson, J. Am. Chem. Soc. 1947, 69, 3002-3004.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 3002-3004
    • Wilson, C.L.1
  • 29
  • 31
    • 0000957901 scopus 로고
    • (Ed.: Z. Rappoport), John Wiley & Sons, Chichester, chapter 9
    • For a detailed recent discussion of cyclopropane stereoisomerizations see: J. E. Baldwin in The Chemistry of the Cychpropyl Group, vol. 2 (Ed.: Z. Rappoport), John Wiley & Sons, Chichester, 1995, chapter 9. p. 469-494.
    • (1995) The Chemistry of the Cychpropyl Group , vol.2 , pp. 469-494
    • Baldwin, J.E.1
  • 34
    • 49049129012 scopus 로고
    • For Lewis acid induced cis/trans-isomerizations of donor-acceptor-substituted cyclopropanes see: H.-U. Reißig. I. Böhm, Tetrahedron Lett. 1983, 24, 715-718.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 715-718
    • Reißig, H.-U.1    Böhm, I.2
  • 35
    • 33748963970 scopus 로고    scopus 로고
    • note
    • An alternative mechanism leading to 2c or 2d may involve isomerization of the sickle-formed allyl anion to a U-shaped allyl anion moiety. See discussion for rearrangements of 7a, 9a, and 9b, respectively, and intermediates of type Ec.
  • 36
    • 33748961343 scopus 로고    scopus 로고
    • note
    • An alternative mechanism for isomerizations of cyclopentenes with configurations a or b to those with c or d, respectively, could also be equilibration by deprotonation-protonation at the cyclopentene stage. However, we have no indication that this process is operating under the reaction conditions employed.
  • 42
    • 33748964635 scopus 로고
    • Dissertation, Université Catholique De Louvain-la-Neuve
    • V. Gallez, Dissertation, Université Catholique De Louvain-la-Neuve, 1989.
    • (1989)
    • Gallez, V.1
  • 43
    • 33748971374 scopus 로고    scopus 로고
    • note
    • [4].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.