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Volumn 47, Issue 37, 2006, Pages 6565-6568

Studies on the deprotonation and subsequent [1,4]-Wittig rearrangement of α-benzyloxyallylsilanes

Author keywords

1,4 Wittig rearrangement; Carbanion; Deprotonation; Organosilanes

Indexed keywords

PROTON; SILANE DERIVATIVE;

EID: 33746796261     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.018     Document Type: Article
Times cited : (12)

References (19)
  • 2
    • 0000135630 scopus 로고
    • For Wittig rearrangement reviews see:
    • For Wittig rearrangement reviews see:. Nakai T., and Mikami K. Org. React. 46 (1994) 105-209
    • (1994) Org. React. , vol.46 , pp. 105-209
    • Nakai, T.1    Mikami, K.2
  • 3
    • 33645791244 scopus 로고    scopus 로고
    • Rappoport Z., and Ilan M. (Eds), Wiley, London
    • Tomooka K. In: Rappoport Z., and Ilan M. (Eds). Chemistry of Organolithium Compounds Vol. 2 (2004), Wiley, London 749-828
    • (2004) Chemistry of Organolithium Compounds , vol.2 , pp. 749-828
    • Tomooka, K.1
  • 4
    • 0001969076 scopus 로고
    • and references cited therein
    • Felkin H., and Frajerman C. Tetrahedron Lett. 18 (1977) 3485-3488 and references cited therein
    • (1977) Tetrahedron Lett. , vol.18 , pp. 3485-3488
    • Felkin, H.1    Frajerman, C.2
  • 11
    • 33746796891 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, as well as appropriate parent ion identification by HRMS. See Supplementary data for additional details.
  • 14
    • 33746826249 scopus 로고    scopus 로고
    • note
    • 1,2-strain within 5 accounts for the seemingly slow intermolecular deprotonation of the allylic protons.
  • 15
    • 0033533643 scopus 로고    scopus 로고
    • 2O)) and 12 (17% (Lewis acid = TMSOTf)) were generated from the corresponding trichloroacetimidate as generally described in and the Supplementary data
    • 2O)) and 12 (17% (Lewis acid = TMSOTf)) were generated from the corresponding trichloroacetimidate as generally described in. Maleczka Jr. R.E., and Geng F. Org. Lett. 1 (1999) 1111-1113 and the Supplementary data
    • (1999) Org. Lett. , vol.1 , pp. 1111-1113
    • Maleczka Jr., R.E.1    Geng, F.2
  • 16
    • 0002092942 scopus 로고
    • For the deprotonation and rearrangement of vinylogous α-alkoxysilanes see:
    • For the deprotonation and rearrangement of vinylogous α-alkoxysilanes see:. Mikami K., Kishi N., and Nakai T. Chem. Lett. (1989) 1683-1686
    • (1989) Chem. Lett. , pp. 1683-1686
    • Mikami, K.1    Kishi, N.2    Nakai, T.3
  • 18
    • 33751385140 scopus 로고
    • It is difficult to estimate the pK differences between 11 and 12, but intrinsic silyl stabilization is said to be worth about 2-3 pK units for delocalized carbon acids. See
    • It is difficult to estimate the pK differences between 11 and 12, but intrinsic silyl stabilization is said to be worth about 2-3 pK units for delocalized carbon acids. See. Streitwieser A., Xie L., Wang P., and Bachrach S.M. J. Org. Chem. 58 (1993) 1778-1784
    • (1993) J. Org. Chem. , vol.58 , pp. 1778-1784
    • Streitwieser, A.1    Xie, L.2    Wang, P.3    Bachrach, S.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.