메뉴 건너뛰기




Volumn 20, Issue 16, 2001, Pages 3574-3581

Organic synthesis via transition metal complexes. 112. Reactivity enhancement of group VI Fischer carbene complexes by copper and rhodium catalysts: Experimental proof of a carbene rhodium complex as an intermediate

Author keywords

[No Author keywords available]

Indexed keywords

FISCHER CARBENE COMPLEXES; RHODAOCTATETRAENE; TUNGSTAOCTATETRAENES; VINYLCYCLOPENTADIENES;

EID: 0035817673     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0103207     Document Type: Article
Times cited : (44)

References (80)
  • 5
    • 0000134379 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York; Chapter 5.3
    • (b) Wulff, W. In Comprehensive Organometallic Chemistry, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York 1995; Vol. 12, Chapter 5.3
    • (1995) Comprehensive Organometallic Chemistry , vol.12
    • Wulff, W.1
  • 6
    • 0346265937 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York; Chapter 5.1 and 5.2
    • (c) Doyle, M. P. In Comprehensive Organometallic Chemistry, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York 1995; Vol. 12, Chapters 5.1 and 5.2.
    • (1995) Comprehensive Organometallic Chemistry , vol.12
    • Doyle, M.P.1
  • 38
    • 0000936113 scopus 로고    scopus 로고
    • note
    • The appearance of a 1-rhoda(II)-1,3,5-hexatriene species, obtained from a o-dialkynyl-substituted diazoacetophenone and catalytic rhodium(II) octanoate and subsequent π-cyclization to a cyclopentadiene, was postulated by: (a) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642-1652.
    • (1997) J. Org. Chem. , vol.62 , pp. 1642-1652
    • Padwa, A.1    Kassir, J.M.2    Xu, S.L.3
  • 39
    • 0002198862 scopus 로고    scopus 로고
    • note
    • For a general review of (related) rhodium(II)-mediated cyclizations involving carbene rhodium complexes obtained from diazo compounds see: (b) Padwa, A. J. Organomet. Chem. 2000; 610, 88-101.
    • (2000) J. Organomet. Chem. , vol.610 , pp. 88-101
    • Padwa, A.1
  • 42
    • 0033986474 scopus 로고    scopus 로고
    • For the chemistry of 1-metalla-1,3,5-hexatrienes see: (a) Aumann, R. Eur. J. Org. Chem. 2000, 17-31.
    • (2000) Eur. J. Org. Chem. , pp. 17-31
    • Aumann, R.1
  • 56
    • 0011439041 scopus 로고    scopus 로고
    • note
    • Compounds 14b-d were obtained in 82-86% yields, whereas compounds 14a was obtained in 48% yield together with a second isomer in 33% yield. For a detailed discussion see ref 1.
  • 57
    • 0011396222 scopus 로고    scopus 로고
    • note
    • 2O)/MeOH an more active catalyst but due to formation of HCl only applicable on acid resistant systems: see ref 9.
  • 58
    • 0000399376 scopus 로고
    • note
    • Carbene rhodium complexes of the type Rh=C(OR)C are not reported to our knowledge; those of the type Rh=C(OM)C are scarcely reported: (a) Erker, G.; Lecht, R.; Tsay, Y.-H.; Krüger, C. Chem. Ber. 1987, 120, 1763-1765.
    • (1987) Chem. Ber. , vol.120 , pp. 1763-1765
    • Erker, G.1    Lecht, R.2    Tsay, Y.-H.3    Krüger, C.4
  • 72
    • 0011490298 scopus 로고    scopus 로고
    • note
    • For a detailed discussion of chemical exchange phenomena in compounds 14 see ref 1.
  • 73
    • 37049132144 scopus 로고
    • note
    • For a discussion of the rotation parameters of the Rh=C bond in N-heterocyclic carbene rhodium complexes see: Doyle, M. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 679-680.
    • (1974) J. Chem. Soc., Chem. Commun. , pp. 679-680
    • Doyle, M.J.1    Lappert, M.F.2
  • 74
    • 0011396078 scopus 로고    scopus 로고
    • note
    • 13C chemical shift of the Rh=C bond. X-ray data are provided in refs 18b-f.
  • 75
    • 0011488503 scopus 로고    scopus 로고
    • note
    • +. In fact the zwitterionic character of tungstaoctatraenes 14 due to the electron-withdrawing CO ligands should be higher than that of compound 16c.
  • 77
    • 0011393737 scopus 로고    scopus 로고
    • (b) References 18b-f
    • (b) References 18b-f.
  • 78
    • 0011490299 scopus 로고    scopus 로고
    • note
    • The mass spectrometer LAZARUS III DE was provided by Dr. H. Luftmann, Organisch-Chemisches Institut der Universität Münster. Data sets were collected with LeCroy DSO 9450A instrumentation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.