Skip to main content
Log in

Synthesis and molecular structure of 4,4,5,5-tetramethyl-2-(1-(phenylsulfonyl)propan-2-yl)-1,3,2-dioxaborolane

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

The compound 4,4,5,5-tetramethyl-2-(1-(phenylsulfonyl)propan-2-yl)-1,3,2-dioxabo- rolane has been prepared by the rhodium catalyzed hydroboration of allyl phenyl sulfone and characterized by a single crystal X-ray diffraction study. The title compound crystallized in the monoclinic space group P21/c, with cell parameters a=16.0728(8) Å, b=9.8884(5) Å, and c=10.1926(5) Å, β=92.067(1)°, Z=4, and V=1618.90(14) Å3. The structure was solved by direct methods and refined to a final R=0.0449 for 3627 reflections with I>2σ(I). No significant intramolecular or intermolecular interaction is observed with the Lewis acidic boron atom.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.
Fig. 2.

Similar content being viewed by others

References

  1. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.

    Article  CAS  Google Scholar 

  2. Carboni, B.; Pourbaix, C.; Carreaux, F.; Deleuze, H.; Maillard, B. Tetrahedron Lett. 1999, 40, 7979.

    Article  CAS  Google Scholar 

  3. Farfan, N.; Höpfl, H.; Barba, V.; Ochoa, M.E.; Santillan, R.; Gomez, E.; Gutierrez, A. J. Organomet. Chem. 1999, 581, 70.

    Article  Google Scholar 

  4. Minutolo, F.; Katzenellenbogen, J.A. Organometallics 1999, 18, 2519.

    Article  CAS  Google Scholar 

  5. Batey, R.A.; MacKay, D.B.; Santhakumar, V. J. Am. Chem. Soc. 1999, 121, 5075.

    Article  CAS  Google Scholar 

  6. Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron 1998, 54, 3125.

    Article  CAS  Google Scholar 

  7. Yang, W.; Gao, X.; Wang, B. Med. Res. Rev. 2003, 23, 346.

    Article  CAS  Google Scholar 

  8. Adams, J. Curr. Opin. Chem. Biol. 2002, 6, 493.

    Article  CAS  Google Scholar 

  9. Carter, C.A.G.; Vogels, C.M.; Harrison, D.J.; Gagnon, M.K.J.; Norman, D.W.; Langler, R.F.; Baker, R.T.; Westcott, S.A. Organometallics 2001, 20, 2130.

    Article  CAS  Google Scholar 

  10. Cremlyn, R. J. In An Introduction to Organosulfur Chemistry. Wiley, Chichester, U.K., 1996.

    Google Scholar 

  11. Irving, A.M.; Vogels, C.M.; Nikolcheva, L.G.; Edwards, J.P.; He, X.-F.; Hamilton, M.G.; Baerlocher, M.O.; Baerlocher, F.J.; Decken, A.; Westcott, S.A. New. J. Chem. 2003, 27, 1419.

    Article  CAS  Google Scholar 

  12. SAINT 6.02, Bruker AXS, Inc., Madison, Wisconsin, USA, 1997–1999.

  13. Sheldrick, G.M. SADABS, Bruker AXS, Inc., Madison, Wisconsin, USA, 1999.

    Google Scholar 

  14. Sheldrick, G.M. SHELXTL 5.1, Bruker AXS, Inc., Madison, Wisconsin, USA. 1997.

    Google Scholar 

  15. Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Syntheses via Boranes, Wiley-Interscience, New York, 1975.

    Google Scholar 

  16. Männig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878.

    Article  Google Scholar 

  17. For reviews on the metal catalysed hydroboration reaction, see: (a) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957. (b) Crudden, C.M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695 and references therein.

  18. Kadlecek, D.E.; Carroll, P.J.; Sneddon, L.G. J. Am. Chem. Soc. 2000, 122, 10868.

    Article  CAS  Google Scholar 

  19. Demay, S.; Volant, F.; Knochel, P. Angew. Chem. Int. Ed. Engl. 2001, 40, 1235.

    Article  CAS  Google Scholar 

  20. Widauer, C.; Grützmacher, H.; Ziegler, T. Organometallics 2000, 19, 2097.

    Article  CAS  Google Scholar 

  21. Hou, X-L.; Hong, D-G.; Rong, G-B.; Guo, Y-L.; Dai, L-X. Tetrahedron Lett. 1993, 34, 8513.

    Article  CAS  Google Scholar 

  22. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Springer-Verlag, Berlin, 1978.

    Google Scholar 

  23. Hawkeswood, S.; Stephan, D.W. Dalton Trans. 2005, 2182.

  24. Grünefeld, J.; Kliegel, W.; Rettig, S.J.; Trotter, J. Can. J. Chem. 1999, 77, 439.

    Article  Google Scholar 

  25. Kliegel, W.; Metge, J.; Rettig, S.J.; Trotter, J. Can. J. Chem. 1997, 75, 1203.

    Article  CAS  Google Scholar 

  26. Wolf, W.M. Acta Crystallogr. B 2001, 57, 54.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Thanks are gratefully extended to the American Chemical Society-Petroleum Research Fund (Grant #37824-B1), Canada Research Chairs Programme, Canadian Foundation for Innovation-Atlantic Innovation Fund, Natural Science and Engineering Research Council of Canada, Los Alamos National Labs, and Mount Allison University for financial support. We also thank Dan Durant and Roger Smith for their expert technical assistance.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Stephen A. Westcott.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Coombs, R.R., Vogels, C.M., Wheaton, S.L. et al. Synthesis and molecular structure of 4,4,5,5-tetramethyl-2-(1-(phenylsulfonyl)propan-2-yl)-1,3,2-dioxaborolane. J Chem Crystallogr 36, 661–665 (2006). https://doi.org/10.1007/s10870-006-9114-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-006-9114-4

KEY WORDS:

Navigation