메뉴 건너뛰기




Volumn 76, Issue 4, 2011, Pages 1086-1099

Selectivity control in alkylidene carbene-mediated C-H insertion and allene formation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENES; C-H BOND; C-H INSERTION; CARBENE INSERTION; CARBENES; CHEMOSELECTIVE; ELECTRONIC EFFECTS; INTERMOLECULAR REACTIONS; SELECTIVITY CONTROL; STEREOELECTRONIC EFFECT; STERIC EFFECT; TRIMETHYLSILYLDIAZOMETHANE;

EID: 79951599212     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102180f     Document Type: Article
Times cited : (28)

References (153)
  • 1
    • 33947094631 scopus 로고
    • For reviews, see
    • For reviews, see: Stang, P. J. Chem. Rev. 1978, 78, 383
    • (1978) Chem. Rev. , vol.78 , pp. 383
    • Stang, P.J.1
  • 2
    • 0001331380 scopus 로고
    • Helmchen G. 4th ed.;, Ed.; Georg Thieme Verlag: New York
    • Taber, D. F. In Methods of Organic Chemistry, 4th ed.; Helmchen, G., Ed.; Georg Thieme Verlag: New York, 1995; Vol. E21, p 1127.
    • (1995) Methods of Organic Chemistry , vol.21 , pp. 1127
    • Taber, D.F.1
  • 8
    • 0003760097 scopus 로고
    • Sapse A.-M. Schleyer P.v.R. Eds.; Wiley: New York, pp , see p 491.
    • Maercker, A. In Lithium Chemistry; Sapse, A.-M.; Schleyer, P. v. R., Eds.; Wiley: New York, 1995; pp 477-577, see p 491.
    • (1995) Lithium Chemistry , pp. 477-577
    • Maercker, A.1
  • 20
    • 0002833170 scopus 로고
    • For selected examples of the formation of 2,5-dihydrofurans, see
    • For selected examples of the formation of 2,5-dihydrofurans, see: Buxton, S. R.; Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1987, 28, 2167
    • (1987) Tetrahedron Lett. , vol.28 , pp. 2167
    • Buxton, S.R.1    Holm, K.H.2    Skattebøl, L.3
  • 23
    • 0034001615 scopus 로고    scopus 로고
    • For the study on selectivity in dihydrofuran formation, see: Tetrahedron Lett. 1997, 38, 4927
    • Singh, G.; Vankayalapati, H. Tetrahedron: Asymmetry 2000, 11, 125 For the study on selectivity in dihydrofuran formation, see: Taber, D. F.; Christos, T. E. Tetrahedron Lett. 1997, 38, 4927
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 125
    • Singh, G.1    Vankayalapati, H.2    Taber, D.F.3    Christos, T.E.4
  • 37
  • 46
    • 33947483256 scopus 로고
    • The observed selectivity can be ascribed to the differences in bond dissociation energies of the various C-H bonds. For a review see.
    • The observed selectivity can be ascribed to the differences in bond dissociation energies of the various C-H bonds. For a review see: Benson, S. W. J. Chem. Educ. 1965, 42, 502.
    • (1965) J. Chem. Educ. , vol.42 , pp. 502
    • Benson, S.W.1
  • 52
    • 33744994317 scopus 로고    scopus 로고
    • Wang, J. Nature 2006, 441, 358
    • (2006) Nature , vol.441 , pp. 358
    • Wang, J.1
  • 86
    • 22944485617 scopus 로고    scopus 로고
    • Ma, S. Chem. Rev. 2005, 105, 2829
    • (2005) Chem. Rev. , vol.105 , pp. 2829
    • Ma, S.1
  • 88
    • 67650059255 scopus 로고    scopus 로고
    • Georg Thieme Verlag: Stuttgart, Germany, Vol. (Cumulenes and Allenes).
    • Krause, N., Ed. Science of Synthesis; Georg Thieme Verlag: Stuttgart, Germany, 2007; Vol. 44 (Cumulenes and Allenes).
    • (2007) Science of Synthesis , vol.44
    • Krause, N.1
  • 90
    • 15444364740 scopus 로고    scopus 로고
    • Hoffmann-Röder A. Krause N. Hashmi A.S.K. For reviews of allenic structures on natural products, see:, Eds.; Wiley-VCH: Weinheim, Germany, p.
    • For reviews of allenic structures on natural products, see: Krause, N.; Hoffmann-Röder, A. Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 997.
    • (2004) Modern Allene Chemistry , pp. 997
    • Krause, N.1
  • 92
    • 50249176474 scopus 로고    scopus 로고
    • For recent examples for allene synthesis, see
    • For recent examples for allene synthesis, see: Pu, X.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 10874
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10874
    • Pu, X.1    Ready, J.M.2
  • 104
  • 105
    • 0002020843 scopus 로고    scopus 로고
    • For selected examples of N-H insertion, see
    • For selected examples of N-H insertion, see: Miyagi, T.; Aoyama, T.; Shioiri, T. Synlett 1997, 1063
    • (1997) Synlett , pp. 1063
    • Miyagi, T.1    Aoyama, T.2    Shioiri, T.3
  • 108
    • 77952406602 scopus 로고    scopus 로고
    • For an example of C-Si insertion, see
    • For an example of C-Si insertion, see: Li, J.; Sun, C.; Lee, D. J. Am. Chem. Soc. 2010, 132, 6640
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6640
    • Li, J.1    Sun, C.2    Lee, D.3
  • 109
    • 0034710466 scopus 로고    scopus 로고
    • For selected examples of O-Si insertion, see
    • For selected examples of O-Si insertion, see: Feldman, K. S.; Wrobleski, M. L. Org. Lett. 2000, 2, 2603
    • (2000) Org. Lett. , vol.2 , pp. 2603
    • Feldman, K.S.1    Wrobleski, M.L.2
  • 113
    • 20044390256 scopus 로고    scopus 로고
    • This can be considered as a Thorp-Ingold effect induced by the two lone-pair electrons of oxygen. For a review and leading references for the Thorpe-Ingold effect, see
    • This can be considered as a Thorp-Ingold effect induced by the two lone-pair electrons of oxygen. For a review and leading references for the Thorpe-Ingold effect, see: Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735
    • (2005) Chem. Rev. , vol.105 , pp. 1735
    • Jung, M.E.1    Piizzi, G.2
  • 125
    • 4644352301 scopus 로고    scopus 로고
    • Selectivity control by changing reaction concentration was demonstrated in olefin metathesis reactions
    • Selectivity control by changing reaction concentration was demonstrated in olefin metathesis reactions: Maifeld, S. V.; Miller, R. L.; Lee, D. J. Am. Chem. Soc. 2004, 126, 12228
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12228
    • Maifeld, S.V.1    Miller, R.L.2    Lee, D.3
  • 126
    • 79951654410 scopus 로고    scopus 로고
    • Instead of free carbene, a protocol that involves carbenoid formation was also examined but the ratio remained unchanged.
    • Instead of free carbene, a protocol that involves carbenoid formation was also examined but the ratio remained unchanged.
  • 136
    • 79951648952 scopus 로고    scopus 로고
    • This is probably due to the difference of strength of C-H bonds on 3-and 5-membered rings. Alternatively, the more favourable n(O)→σ (C-H) electron delocalization in dioxolane may also cause this difference as described in ref 13a.
    • This is probably due to the difference of strength of C-H bonds on 3-and 5-membered rings. Alternatively, the more favourable n(O)→σ(C-H) electron delocalization in dioxolane may also cause this difference as described in ref 13a.
  • 137
    • 0028125319 scopus 로고
    • For other representative examples of allenylsilane synthesis and their use in organic synthesis, see
    • For other representative examples of allenylsilane synthesis and their use in organic synthesis, see: Borzilleri, R. M.; Weinreb, S. M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9789
    • Borzilleri, R.M.1    Weinreb, S.M.2    Parvez, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.