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Synthesis and molecular structure of the organometallic zwitterion (η5-C5H3MeBCl3)Fe(CO)3: evidence for alternative sites of nucleophilicity within the [(η5-C5R5)Fe(CO)2 anion

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Abstract

The organometallic zwitterion (η5-C5H3MeBCl3)Fe(CO)3 (2) is isolated as a minor product from the reaction between the sodium salt of the anion [(η5-C5H4Me)Fe(CO)2] and boron trichloride. The crystal structure of 2 [P21/n, a = 7.3927(5) Å, b = 13.8027(9) Å, c = 12.2759(9) Å, α =γ = 90°, β = 92.517(3)°] features discrete molecules in which the coordination sphere of the iron center comprises three carbonyls and a novel (η 5-C5H3MeBCl3) ligand, derived from attack of BCl3 on the (η 5-C5H4Me) moiety of the parent compound. The isolation of 2 confirms that the nucleophilic properties of organometallic anions of the type [(η 5-C5R5)M(CO) n ] (M = Fe, Ru, n = 2; M = Mo, W, n = 3) are not confined to the metal center, or to the carbonyl oxygens (examples of which have previously been reported) but also encompass the cyclopentadienyl ligand.

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References

  • Irvine, G.J.; Lesley, M.J.G.; Marder, T.B.; Norman, N.C.; Rice, C.R.; Robins, E.G.; Roper, W.R.; Whittell, G.R.; Wright, L.J. Chem. Rev. 1998, 98, 2685.

    PubMed  Google Scholar 

  • Smith, M.R. Prog. Inorg. Chem. 1999, 48, 505.

    Google Scholar 

  • Braunschweig, H. Coord. Chem. Rev. 2001, 223, 1.

    Google Scholar 

  • Brown, H.C.; Singaram, B. Pure Appl. Chem. 1987, 59, 879.

    Google Scholar 

  • Burgess, K.; Ohlmeyer, M.J. Chem. Rev. 1991, 91, 1179.

    Google Scholar 

  • Iverson, C.; Smith, M.R. Organometallics 1996, 15, 5155.

    Google Scholar 

  • Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.

    Google Scholar 

  • Marder, T.B.; Norman, N.C. Top. Catal. 1998, 5, 63.

    Google Scholar 

  • Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.

    Google Scholar 

  • Waltz, K.M.; He, X.; Muhoro, C.; Hartwig, J.F. J. Am. Chem. Soc. 1995, 117, 11357.

    Google Scholar 

  • Waltz, K.M.; Hartwig, J.F. Science 1997, 277, 211.

    Google Scholar 

  • Waltz, K.M.; Muhoro, C.N.; Hartwig, J.F. Organometallics 1999, 18, 3383.

    Google Scholar 

  • Waltz, K.M.; Hartwig, J.F. J. Am. Chem. Soc. 2000, 122, 11358.

    Google Scholar 

  • Kawamura, K.; Hartwig, J.F. J. Am. Chem. Soc. 2001 123, 8422.

    PubMed  Google Scholar 

  • Ishiyama, T.; Tagaki, J.; Ishida, K.; Miyaura, N.; Anastasi, N.R.; Hartwig, J.F. J. Am. Chem. Soc. 2002, 124, 390.

    PubMed  Google Scholar 

  • Iverson, C.N.; Smith, M.R. J. Am. Chem. Soc. 1999, 121, 7696.

    Google Scholar 

  • Chen, H.; Hartwig, J.F. Angew. Chem., Int. Ed. Engl. 1999, 38, 3391.

    Google Scholar 

  • Chen, H.; Schlecht, S.; Semple, T.C.; Hartwig, J.F. Science 2000, 287, 1995.

    PubMed  Google Scholar 

  • Shimada, S.; Batsanov, S.; Howard, J.A.K.; Marder, T.B. Angew. Chem., Int. Ed. Engl. 2001, 40, 2168.

    Google Scholar 

  • Cho, J.Y.; Tse, M.K.; Holmes, V; Maleczka, R.E.; Smith, M.R. Science 2002, 295, 305.

    PubMed  Google Scholar 

  • Aldridge, S.; Calder, R.J.; Dickinson, A.A.; Willock, D.J.; Steed, J.W. Chem. Commun. 2000, 1377.

  • Aldridge, S.; Calder, R.J.; Rossin, A.; Dickinson, A.A.; Willock, D.J.; Jones, C.; Evans, D.J.; Steed, J.W.; Light, M.E.; Hursthouse, M.B. J. Chem. Soc., Dalton Trans. 2002, 2020.

  • Aldridge, S.; Al-Fawaz, A.; Calder, R.J.; Dickinson, A.A.; Willock, D.J.; Light, M.L.; Hursthouse, M.B. Chem. Commun. 2001, 1846.

  • Aldridge, S.; Coombs, D.L.; Jones, C. Chem. Commun. 2002, 856.

  • Aldridge, S.; Calder, R.J.; Baghurst, R.E.; Light, M.E.; Hursthouse, M.B. J. Organomet. Chem. 2002, 694, 9.

    Google Scholar 

  • King, R.B.; Bisnette, M.B. J. Organomet. Chem. 1967, 8, 287.

    Google Scholar 

  • King, R.B. Acc. Chem. Res. 1970, 3, 417.

    Google Scholar 

  • Otwinowski, Z.; Minor, W. In Methods in Enzymology; Carter, C.W.; Sweet, R.M., Eds.; Academic Press: New York. 1996; Vol. 276, p. 307.

    Google Scholar 

  • Hooft, R. Nonius BV, Delft, The Netherlands, 1997.

    Google Scholar 

  • Sheldrick, G.M. Acta Cryst. A 1990, 46, 467.

    Article  Google Scholar 

  • Braunschweig, H.; Wagner, T. Chem. Ber. 1994, 127, 1613.

    Google Scholar 

  • Burlitch, J.M.; Burk, J.H.; Leonowicz, M.E.; Hughes, R.E. Inorg. Chem. 1979, 18, 1702.

    Google Scholar 

  • Doerrer, L.H.; Graham, A.J.; Haussinger, D.; Green, M.L.H. J. Chem. Soc., Dalton Trans. 2000, 813.

  • Gress, M.E.; Jacobsen, R.A. Inorg. Chem. 1973, 12, 1746.

    Google Scholar 

  • Braunschweig, H.; Koster, M.; Klinkhammer, K.W. Angew. Chem., Int. Ed. Engl. 1999, 38, 2229.

    Google Scholar 

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Aldridge, S., Calder, R.J., Coles, S.J. et al. Synthesis and molecular structure of the organometallic zwitterion (η5-C5H3MeBCl3)Fe(CO)3: evidence for alternative sites of nucleophilicity within the [(η5-C5R5)Fe(CO)2 anion. Journal of Chemical Crystallography 33, 805–808 (2003). https://doi.org/10.1023/A:1026167626120

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