Skip to main content
SpringerLink
Log in

The synthesis and structural characterization of silyl-substituted fluorenes

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Three silyl-substituted fluorenes have been prepared by direct synthetic methods and structurally characterized by X-ray diffraction. The three silyl-substituted fluorenes studied were 9-trimethylsilylfluorene (1), 9-(tert-butyldimethyl)silylfluorene (2), and 2,7-di-tert-butyl-9-trimethylsilylfluorene (3). Complex 1 is orthorhombic, P212121, a = 6.2681(14) Å, b = 14.329(3) Å, c = 15.231(4) Å, Z = 4. Complex 2 is monoclinic, P21/c, a = 12.1953(10) Å, b = 6.9977(6) Å, c = 19.6536(17) Å, β = 93.818(2)○, Z = 4. Complex 3 is monoclinic, P21/c, a = 11.9954(9) Å, b = 9.8978(7) Å, c = 18.5464(13) Å, β = 92.456(2)○, Z = 4. The long carbon–silicon bonds effectively remove any significant intramolecular interactions as little distortion is exhibited around the sp 3-carbon atom and the fluorenyl backbone demonstrates near planarity. The bulky silicon substituents also prevent intermolecular interactions, as only a few close contacts less than 4.0 Å exist in all three solid state structures.

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. O'Connor, J.M.; Casey, C.P. Chem. Rev. 1987, 87, 307.

    Google Scholar 

  2. Biagioni, R.N.; Lorkovic, I.M.; Skelton, J.; Hartung, J.B. Organometallics 1990, 9, 547.

    Google Scholar 

  3. Halterman, R.L. In Metallocenes; Togni, A.; Halterman, R.L., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, p 520.

    Google Scholar 

  4. Samuel, E.; Setton, R. J. Organomet. Chem. 1965, 4, 156.

    Google Scholar 

  5. Samuel, E.; Alt, H.G.; Hrncir, D.C.; Rausch, M.D. J. Organomet. Chem. 1976, 113, 331.

    Google Scholar 

  6. Harder, S.; Feil, F.; Knoll, K. Angew. Chem., Int. Ed. 2001, 40, 4261.

    Google Scholar 

  7. Schmid, M.A.; Alt, H.G.; Milius, W. J. Organomet. Chem. 1996, 525, 15.

    Google Scholar 

  8. Nakamura, H.; Nakayama, Y.; Yasuda, H.; Maruo, T.; Kanehisa, N.; Kai, Y. Organometallics 2000, 19, 5392.

    Google Scholar 

  9. Constantine, S.P.; Hitchcock, P.B.; Lawless, G.A. Organometallics 1996, 15, 3905.

    Google Scholar 

  10. Constantine, S.P.; Cox, H.; Hitchcock, P.B.; Lawless, G.A. Organometallics 2000, 19, 317.

    Google Scholar 

  11. Carpino, L.A.; Wu, A.-C. U.S. Patent 5,101,059 1991.

  12. Stigers, K.D.; Koutroulis, M.R.; Chung, D.M.; Nowick, J.S. J. Org. Chem. 2000, 65, 3858.

    PubMed  Google Scholar 

  13. Carpino, L.A.; Wu, A.-C. J. Org. Chem. 2000, 65, 9238.

    PubMed  Google Scholar 

  14. Silaghi-Dumitrescu, L.; Haiduc, I.; Escudie, J.; Couret, C.; Satge, J. Synth. React. Inorg. Met.-Org. Chem. 1995, 25, 575.

    Google Scholar 

  15. Sheldrick, G.M.; Dauter, Z.; Wilson, K.S.; Hope, H.; Sieker, L.C. Acta Crystallogr. D 1993, 49, 18.

    PubMed  Google Scholar 

  16. Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.

    Google Scholar 

  17. Karczmarzyk, Z.; Mojzych, M.; Rykowski, A. J. Chem. Crystallogr. 2000, 30, 423.

    Google Scholar 

  18. Knjazhanski, S.Y.; Moreno, G.; Cadenas, G.; Belsky, V.K.; Bulychev, B.M. Tetrahedron 1999, 55, 1639.

    Google Scholar 

  19. Zaitseva, G.S.; Karlov, S.S.; Siggelkow, B.A.; Avtomonov, E.V.; Churakov, A.V.; Howard, J.A.K.; Lorberth, J. Z. Naturforsch, B: Chem. Sci. 1998, 53, 1247.

    Google Scholar 

  20. Rengstl, A.; Schuber, U. Chem. Ber. 1980, 113, 278.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, College of Charleston, Charleston, South Carolina, 29424

    Jason S. Overby, Richard T. Woofter, Christopher D. Incarvito & Roger D. Sommer

  2. Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware, 19716

    Arnold L. Rheingold

Authors
  1. Jason S. Overby
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Richard T. Woofter
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Arnold L. Rheingold
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Christopher D. Incarvito
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Roger D. Sommer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jason S. Overby.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Overby, J.S., Woofter, R.T., Rheingold, A.L. et al. The synthesis and structural characterization of silyl-substituted fluorenes. Journal of Chemical Crystallography 33, 357–364 (2003). https://doi.org/10.1023/A:1024221928841

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024221928841

Search

Navigation