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Volumn 48, Issue 45, 2007, Pages 7961-7964

Absence of the Thorpe-Ingold effect by gem-diphenyl groups in ring-closing enyne metathesis

Author keywords

Cyclization; Enyne metathesis; Ring closing metathesis; Silicon; Thorpe Ingold effect

Indexed keywords

BIPHENYL; GOLD;

EID: 35148825025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.063     Document Type: Article
Times cited : (20)

References (33)
  • 1
    • 20044390256 scopus 로고    scopus 로고
    • For a recent review on the 'Thorpe-Ingold effect,' see:
    • For a recent review on the 'Thorpe-Ingold effect,' see:. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735-1766
    • (2005) Chem. Rev. , vol.105 , pp. 1735-1766
    • Jung, M.E.1    Piizzi, G.2
  • 11
    • 1842483218 scopus 로고    scopus 로고
    • For reviews on enyne metathesis, see:
    • For reviews on enyne metathesis, see:. Giessert A.J., and Diver S.T. Chem. Rev. 104 (2004) 1317-1382
    • (2004) Chem. Rev. , vol.104 , pp. 1317-1382
    • Giessert, A.J.1    Diver, S.T.2
  • 14
    • 3042782211 scopus 로고    scopus 로고
    • Grubbs R.H. (Ed), Wiley-VCH, Weinheim
    • Mori M. In: Grubbs R.H. (Ed). Handbook of Metathesis Vol. 2 (2003), Wiley-VCH, Weinheim 176-204
    • (2003) Handbook of Metathesis , vol.2 , pp. 176-204
    • Mori, M.1
  • 18
    • 10044283190 scopus 로고    scopus 로고
    • For the preparation of unsymmetrical silaketals, see Ref. 5; also:
    • For the preparation of unsymmetrical silaketals, see Ref. 5; also:. Grimm J.B., and Lee D. J. Org. Chem. 69 (2004) 8967-8970
    • (2004) J. Org. Chem. , vol.69 , pp. 8967-8970
    • Grimm, J.B.1    Lee, D.2
  • 20
    • 35148895557 scopus 로고    scopus 로고
    • note
    • + 345.1863, found 345.1862.
  • 30
    • 35148851676 scopus 로고    scopus 로고
    • note
    • Deducing from the decoupling experiment, we conclude that the single siloxane product resulting from the RCM of 6a must be 8a, which results from the initial enyne RCM of the longer, unsubstituted alkene tether of 6a. Furthermore, in order to systematically interpret the ratio of the mixture of two bicycles obtained from the concentration-dependent studies, we were able to utilize the chemical shift and splitting patterns observed for the vinyl protons β to the silicon that were distinct between that in a six-membered ring and that in a seven-membered ring (i.e., 7a vs 8a). Notably, the splitting patterns for this downshifted vinyl proton signals were consistent among the different products and therefore allowed a simple and reliable assignment of the ratios of the chromatographically inseparable mixture of the two bicycles.
  • 33
    • 0000365939 scopus 로고
    • To the best of our knowledge, only one example of gem-diphenyl effect in a ring-closure reaction is known. In this case the expected rate enhancement was observed. See:
    • To the best of our knowledge, only one example of gem-diphenyl effect in a ring-closure reaction is known. In this case the expected rate enhancement was observed. See:. Brown R.F., and van Gulick N.M. J. Org. Chem. 21 (1956) 1046-1049
    • (1956) J. Org. Chem. , vol.21 , pp. 1046-1049
    • Brown, R.F.1    van Gulick, N.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.