Skip to main content
SpringerLink
Log in

Reactions of [Re(NO)2(PR3)2][BArF 4] complexes with phenylacetylene

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction of [Re(NO)2(PR3)2][BArF 4] (R = cyclo-C6H13 (1a), Pri (1b); [BArF 4]– = [B(3,5-(CF3)2C6H3)4]) with phenylacetylene in the presence of a non-nucleophilic base, like 2,6-bis(tert-butyl)pyridine (BTBP) or ButOK, affords the phenylethynyl complexes [Re(C≡CPh)(NO)2(PR3)2] (R = cyclo-C6H13 (2a); Pri (2b)) in moderate yields. In the absence of a base, complexes 1a and 1b are transformed into the compounds [Re(C≡CPh)(CH=C(Ph)ONH)(NO)(PR3)2][BArF 4] (3a and 3b, respectively). The structure of complex 3a was confirmed by X-ray diffraction analysis. The latter reaction is proposed to be initiated by deprotonation of the terminal alkyne H atom by the bent nitrosyl ligand followed by the subsequent 1,3-dipolar addition of the ReN(H)O moiety to phenylacetylene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) W. T. Boese and A. S. Goldman, Organometallics, 1991, 10, 782; (b) I. P. Kovalev, K. V. Yerdakov, Yu. A. Strelenko, M. G. Vinogradov, and G. I. Nikishin, J. Organomet. Chem., 1990, 386, 139; (c) T. Ohmura, S. Yorozuya, Y. Yamamoto, and N. Miyaura, Organometallics, 2000, 19, 365; (d) R. Nast, Coord. Chem. Rev., 1982, 47, 89; (e) D. R. Senn, A. Wong, A. T. Patton, M. Marsi, C. E. Strouse, and J. A. Gladysz, J. Am. Chem. Soc., 1988, 110, 6096; (f) J. J. Kowalczyk, A. M. Arif, and J. A. Gladysz, Organometallics, 1991, 10, 1079; (g) J. A. Ramdsen, W. Q. Wenig, and J. A. Gladysz, Organometallics, 1992, 11, 3536.

    Google Scholar 

  2. (a) M. Yoshida, R. F. Jordan, Organometallics, 1997, 16, 4508; (b) A. D. Horton, J. Chem. Soc., Chem. Commun., 1992, 185; (c) C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 1996, 15, 5275; (d) M. Schaefer, N. Mahr, J. Wolf, and H. Werner, Angew. Chem., Int. Ed. Engl., 1993, 32, 1315.

    Google Scholar 

  3. (a) Y. Wakatsuki, N. Koga, H. Yamazaki, and K. Morokuma, J. Am. Chem. Soc., 1994, 116, 8105; (b) I. de los Rios, M. J. Tenorio, M. C. Puerta, and P. Valerga, J. Am. Chem. Soc., 1997, 119, 6529; (c) R. Stegmann and G. Frenking, Organo-metallics, 1998, 17, 2089; (d) E. Peréz-Carreno, P. Paoli, A. Ienco, and C. Mealli, Eur. J. Inorg. Chem., 1999, 1315; (e) C. Garcýa-Yebra, C. Lopez-Mardomingo, M. Fajardo, A. Antinolo, A. Otereo, A. Rodrýguez, A. Vallat, D. Lucas, Y. Mugnier, J. J. Carbo, A. Lledos, and C. Bo, Organometallics, 2000, 19, 1749; (f) E. Bustelo, I. de los Rios, M. J. Tenorio, M. C. Puerta, and P. Valerga, Monatsheft. Chem., 2000, 131, 1311; (g) E. Bustelo, M. Jimenez-Tenorio, M. C. Puerta, and P. Valerga, Eur. J. Inorg. Chem., 2001, 2391; (h) H. Werner, Angew. Chem., Int. Ed. Engl., 1990, 29, 1077.

    Google Scholar 

  4. (a) S. J. Landon, P. M. Shulman, and G. L. Geoffroy, J. Am. Chem. Soc., 1985, 107, 6739; (b) R. Maché, Y. Sasaki, C. Bruneau, and P. H. Dixneuf, J. Org. Chem., 1989, 54, 1518; (c) B. M. Trost, G. Dyker, and R. J. Kulawiec, J. Am. Chem. Soc., 1990, 112, 7809; (d) C. Bianchini, M. Peruzzini, F. Zanobini, P. Frediani, and A. Albinati, J. Am. Chem. Soc., 1991, 113, 5453.

    Google Scholar 

  5. H. Jacobsen, K. Heinze, A. Llamazares, H. W. Schmalle, G. Artus, and H. Berke, J. Chem. Soc., Dalton Trans., 1999, 1717.

  6. (a) Y. Sun, N. J. Taylor, and A. J. Carty, Organometallics, 1992, 11, 101; (b) R. D. Markwell, I. S. Butler, A. K. Kakkar, M. S. Kahn, Z. H. Al-Zakwani, and J. Lewis, Organometallics, 1996, 15, 2331; (c) F. Paul, J. Y. Mevellec, and C. Lapinte, J. Chem. Soc., Dalton Trans., 2002, 1783.

    Google Scholar 

  7. D. G. Gusev, A. Llamazares, G. Artus, H. Jacobsen, and H. Berke, Organometallics, 1999, 17, 75.

    Google Scholar 

  8. Stoe IPDS Software for Data Collection, Cell Refinement, and Data Reduction, Version 2.92, Stoe and Cie GmbH, Darmstadt, Germany, 1999.

  9. P. Coppens, L. Leiserowitz, and D. Rabinovich, Acta Crystallogr., 1965, 18, 1035.

    Google Scholar 

  10. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.

    Google Scholar 

  11. A. L. Spek, Acta Crystallogr., Sect. A, 1990, 46, C-34.

    Google Scholar 

  12. Y. Le Page, J. Appl. Crystallogr., 1987, 20, 264.

    Google Scholar 

  13. G. M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen, Germany, 1997.

    Google Scholar 

  14. C. K. Johnson, ORTEPII, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1976.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Inorganic Chemistry, University of Zurich, 8057, Zurich, Switzerland

    C. M. Frech, A. Llamazares, M. Alfonso, H. W. Schmalle & H. Berke

Authors
  1. C. M. Frech
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Llamazares
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Alfonso
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. W. Schmalle
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. Berke
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Frech, C.M., Llamazares, A., Alfonso, M. et al. Reactions of [Re(NO)2(PR3)2][BArF 4] complexes with phenylacetylene. Russian Chemical Bulletin 53, 1116–1120 (2004). https://doi.org/10.1023/B:RUCB.0000041309.19570.1d

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUCB.0000041309.19570.1d

Search

Navigation