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Volumn , Issue 6, 1998, Pages 1011-1022

Chromium complex catalyzed synthesis of spirocyclopropanes from diaryl diazo compounds - Direct NMR-spectroscopic observation of a carbene complex intermediate

Author keywords

Carbene complex; Catalysis; Chromium; Cyclopropanation; Diazo compounds

Indexed keywords


EID: 0001885054     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<1011::AID-EJOC1011>3.0.CO;2-H     Document Type: Article
Times cited : (38)

References (69)
  • 1
    • 15644378136 scopus 로고    scopus 로고
    • (Ed.: E. Müller), Thieme, Stuttgart
    • Reviews: [1a] Methoden Org. Chem. (Hauben-Weyl) 4th. ed. 1952-, Vol. VI/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971. [1b] Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E17a-c (Ed.: A de Meijere), Thieme, Stuttgart, 1997. [1c] J. R. Y. Salaün, Top. Curr. Chem. 1988,144, 1 [1d] H.-U. Reissig, ibid. 1988, 144, 73. - H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165.
    • (1971) Methoden Org. Chem. (Hauben-Weyl) 4th. Ed. 1952 , vol.6 , Issue.3
  • 2
    • 15644378136 scopus 로고    scopus 로고
    • (Ed.: A de Meijere), Thieme, Stuttgart
    • Reviews: [1a] Methoden Org. Chem. (Hauben-Weyl) 4th. ed. 1952-, Vol. VI/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971. [1b] Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E17a-c (Ed.: A de Meijere), Thieme, Stuttgart, 1997. [1c] J. R. Y. Salaün, Top. Curr. Chem. 1988,144, 1 [1d] H.-U. Reissig, ibid. 1988, 144, 73. - H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165.
    • (1997) Methoden Org. Chem. (Houben-Weyl) 4th. Ed. 1952 , vol.E17A-C
  • 3
    • 15644378136 scopus 로고    scopus 로고
    • Reviews: [1a] Methoden Org. Chem. (Hauben-Weyl) 4th. ed. 1952-, Vol. VI/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971. [1b] Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E17a-c (Ed.: A de Meijere), Thieme, Stuttgart, 1997. [1c] J. R. Y. Salaün, Top. Curr. Chem. 1988,144, 1 [1d] H.-U. Reissig, ibid. 1988, 144, 73. - H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165.
    • (1988) Top. Curr. Chem. , vol.144 , pp. 1
    • Salaün, J.R.Y.1
  • 4
    • 15644378136 scopus 로고    scopus 로고
    • Reviews: [1a] Methoden Org. Chem. (Hauben-Weyl) 4th. ed. 1952-, Vol. VI/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971. [1b] Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E17a-c (Ed.: A de Meijere), Thieme, Stuttgart, 1997. [1c] J. R. Y. Salaün, Top. Curr. Chem. 1988,144, 1 [1d] H.-U. Reissig, ibid. 1988, 144, 73. - H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165.
    • (1988) Top. Curr. Chem. , vol.144 , pp. 73
    • Reissig, H.-U.1
  • 5
    • 15644378136 scopus 로고    scopus 로고
    • Reviews: [1a] Methoden Org. Chem. (Hauben-Weyl) 4th. ed. 1952-, Vol. VI/3 (Ed.: E. Müller), Thieme, Stuttgart, 1971. [1b] Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E17a-c (Ed.: A de Meijere), Thieme, Stuttgart, 1997. [1c] J. R. Y. Salaün, Top. Curr. Chem. 1988,144, 1 [1d] H.-U. Reissig, ibid. 1988, 144, 73. - H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165.
    • (1989) Chem. Rev. , vol.89 , pp. 165
    • Wong, H.N.C.1    Hon, M.-Y.2    Tse, C.-W.3    Yip, Y.-C.4    Tanko, J.5    Hudlicky, T.6
  • 7
    • 0019620732 scopus 로고
    • [2a] D Arlt, M. Jautelat, R. Lantzsch, Angew. Chem. 1981, 93, 719: Angew. Chem. Int Ed. Engl. 1981, 20, 703.
    • (1981) Angew. Chem. Int Ed. Engl. , vol.20 , pp. 703
  • 11
    • 0000134379 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York
    • Reviews: [4a] M. P. Doyle, in Comprehensive Organometallic Chemistry 2, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 387. [4b] S. D. Burke, P. A. Gricco, Org. React. 1979, 26, 361. [4c] M. P. Doyle, Chem. Rev. 1986, 86, 919. - [4d] A. Padwa, K E. Krumpe, Tetrahedron 1992, 48, 5385.
    • (1995) Comprehensive Organometallic Chemistry 2 , vol.12 , pp. 387
    • Doyle, M.P.1
  • 12
    • 0000435880 scopus 로고
    • Reviews: [4a] M. P. Doyle, in Comprehensive Organometallic Chemistry 2, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 387. [4b] S. D. Burke, P. A. Gricco, Org. React. 1979, 26, 361. [4c] M. P. Doyle, Chem. Rev. 1986, 86, 919. - [4d] A. Padwa, K E. Krumpe, Tetrahedron 1992, 48, 5385.
    • (1979) Org. React. , vol.26 , pp. 361
    • Burke, S.D.1    Gricco, P.A.2
  • 13
    • 18444417883 scopus 로고
    • Reviews: [4a] M. P. Doyle, in Comprehensive Organometallic Chemistry 2, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 387. [4b] S. D. Burke, P. A. Gricco, Org. React. 1979, 26, 361. [4c] M. P. Doyle, Chem. Rev. 1986, 86, 919. - [4d] A. Padwa, K E. Krumpe, Tetrahedron 1992, 48, 5385.
    • (1986) Chem. Rev. , vol.86 , pp. 919
    • Doyle, M.P.1
  • 14
    • 0026632575 scopus 로고
    • Reviews: [4a] M. P. Doyle, in Comprehensive Organometallic Chemistry 2, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 387. [4b] S. D. Burke, P. A. Gricco, Org. React. 1979, 26, 361. [4c] M. P. Doyle, Chem. Rev. 1986, 86, 919. - [4d] A. Padwa, K E. Krumpe, Tetrahedron 1992, 48, 5385.
    • (1992) Tetrahedron , vol.48 , pp. 5385
    • Padwa, A.1    Krumpe, K.E.2
  • 15
    • 0037599887 scopus 로고
    • (Eds.: G. Heimchen. R. W. Hoffmann, J. Mulzer, E. Schaumann). Thieme, Stuttgart
    • Reviews: [5a] H.-U. Reissig, in Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E21c (Eds.: G. Heimchen. R. W. Hoffmann, J. Mulzer, E. Schaumann). Thieme, Stuttgart, 1995, p. 3179. [5b] A. Pfaltz, Acc. Chem. Res. 1993, 26, 339. [5c] M. P. Doyle in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, 63.
    • (1995) Methoden Org. Chem. (Houben-Weyl) 4th. Ed. 1952 , vol.E21C , pp. 3179
    • Reissig, H.-U.1
  • 16
    • 3242857105 scopus 로고
    • Reviews: [5a] H.-U. Reissig, in Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E21c (Eds.: G. Heimchen. R. W. Hoffmann, J. Mulzer, E. Schaumann). Thieme, Stuttgart, 1995, p. 3179. [5b] A. Pfaltz, Acc. Chem. Res. 1993, 26, 339. [5c] M. P. Doyle in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, 63.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 339
    • Pfaltz, A.1
  • 17
    • 0003544583 scopus 로고
    • (Ed.: I. Ojima), VCH, New York
    • Reviews: [5a] H.-U. Reissig, in Methoden Org. Chem. (Houben-Weyl) 4th. ed. 1952-, Vol. E21c (Eds.: G. Heimchen. R. W. Hoffmann, J. Mulzer, E. Schaumann). Thieme, Stuttgart, 1995, p. 3179. [5b] A. Pfaltz, Acc. Chem. Res. 1993, 26, 339. [5c] M. P. Doyle in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, 63.
    • (1993) Catalytic Asymmetric Synthesis , pp. 63
    • Doyle, M.P.1
  • 18
    • 0001331721 scopus 로고
    • Review: W. A. Herrmann, Angew Chem. 1978, 90, 855; Angew. Chem. Int Ed Engl. 1978, 17, 800.
    • (1978) Angew Chem. , vol.90 , pp. 855
    • Herrmann, W.A.1
  • 19
    • 0018031404 scopus 로고
    • Review: W. A. Herrmann, Angew Chem. 1978, 90, 855; Angew. Chem. Int Ed Engl. 1978, 17, 800.
    • (1978) Angew. Chem. Int Ed Engl. , vol.17 , pp. 800
  • 23
    • 0009582666 scopus 로고    scopus 로고
    • J. Pfeiffer, K. H. Dötz. Angew. Chem. 1997, 109, 2948; Angew. Chem. Int. Ed. Engl. 1997, 36, 2828.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2828
  • 26
    • 84943877929 scopus 로고
    • The uncatalyzed [2 + 1] cycloaddition of diazo compound 1 is known e.g. for methyl acrylate: L. Horner, E. Lingnau, Liebigs Ann. Chem. 1955, 591, 21.
    • (1955) Liebigs Ann. Chem. , vol.591 , pp. 21
    • Horner, L.1    Lingnau, E.2
  • 32
    • 0000726445 scopus 로고    scopus 로고
    • The formation of cyclopentenes via a formal [3 + 2] cycloaddition reaction involving an olefin metathesis has been observed in the stoichiometric reactions of Fischer carbene complexes with donor-acceptor substituted dienes: M. Hoffmann, M. Buchert, H.-U. Reissig, Angew. Chem 1997, 709, 281; Angew. Chem. Int. Ed. Engl. 1997, 36, 283.
    • (1997) Angew. Chem , vol.709 , pp. 281
    • Hoffmann, M.1    Buchert, M.2    Reissig, H.-U.3
  • 33
    • 0030945984 scopus 로고    scopus 로고
    • The formation of cyclopentenes via a formal [3 + 2] cycloaddition reaction involving an olefin metathesis has been observed in the stoichiometric reactions of Fischer carbene complexes with donor-acceptor substituted dienes: M. Hoffmann, M. Buchert, H.-U. Reissig, Angew. Chem 1997, 709, 281; Angew. Chem. Int. Ed. Engl. 1997, 36, 283.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 283
  • 41
    • 2742549693 scopus 로고    scopus 로고
    • IUPAC-IUB Joint Commission on Biochemical Nomenclature, Carbohydr. Res. 1997, 297, 1.
    • (1997) Carbohydr. Res. , vol.297 , pp. 1
  • 42
  • 55
    • 0007537633 scopus 로고
    • D. Rewicki, C. Tuchscherer, Angew. Chem. 1972, 84, 31; Angew. Chem Int Ed. Engl 1972, 11, 44.
    • (1972) Angew. Chem Int Ed. Engl , vol.11 , pp. 44
  • 63
    • 2742609183 scopus 로고    scopus 로고
    • accepted for publication
    • The different propensity for dissociation of a carbon monoxide ligand may also explain the different behaviour of the pentacarbonyl chromium carbene complexes accessible from the diazo precursors 1, 22, 24 and 25 in the benzannulation reaction with 1-hexyne, see ref[16a] and: J. Pfeiffer, M. Nieger, K. H. Dötz, Chem. Eur. J., accepted for publication.
    • Chem. Eur. J.
    • Pfeiffer, J.1    Nieger, M.2    Dötz, K.H.3
  • 67
    • 0004150157 scopus 로고
    • Siemens Analytical X-ray Instruments Inc., Madison, Wi., USA
    • G. M. Sheldrick, SHELXTL-Plus, Siemens Analytical X-ray Instruments Inc., Madison, Wi., USA, 1989.
    • (1989) SHELXTL-Plus
    • Sheldrick, G.M.1
  • 68
    • 0004150157 scopus 로고
    • Universität Göttingen, Germany
    • G. M. Sheldrick, SHELXL-93, Universität Göttingen, Germany, 1993.
    • (1993) SHELXL-93
    • Sheldrick, G.M.1


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