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.
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References
Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
Carboni, B.; Pourbaix, C.; Carreaux, F.; Deleuze, H.; Maillard, B. Tetrahedron Lett. 1999, 40, 7979.
Farfan, N.; Höpfl, H.; Barba, V.; Ochoa, M.E.; Santillan, R.; Gomez, E.; Gutierrez, A. J. Organomet. Chem. 1999, 581, 70.
Minutolo, F.; Katzenellenbogen, J.A. Organometallics 1999, 18, 2519.
Batey, R.A.; MacKay, D.B.; Santhakumar, V. J. Am. Chem. Soc. 1999, 121, 5075.
Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron 1998, 54, 3125.
Yang, W.; Gao, X.; Wang, B. Med. Res. Rev. 2003, 23, 346.
Adams, J. Curr. Opin. Chem. Biol. 2002, 6, 493.
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.
Cremlyn, R. J. In An Introduction to Organosulfur Chemistry. Wiley, Chichester, U.K., 1996.
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.
SAINT 6.02, Bruker AXS, Inc., Madison, Wisconsin, USA, 1997–1999.
Sheldrick, G.M. SADABS, Bruker AXS, Inc., Madison, Wisconsin, USA, 1999.
Sheldrick, G.M. SHELXTL 5.1, Bruker AXS, Inc., Madison, Wisconsin, USA. 1997.
Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Syntheses via Boranes, Wiley-Interscience, New York, 1975.
Männig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878.
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.
Kadlecek, D.E.; Carroll, P.J.; Sneddon, L.G. J. Am. Chem. Soc. 2000, 122, 10868.
Demay, S.; Volant, F.; Knochel, P. Angew. Chem. Int. Ed. Engl. 2001, 40, 1235.
Widauer, C.; Grützmacher, H.; Ziegler, T. Organometallics 2000, 19, 2097.
Hou, X-L.; Hong, D-G.; Rong, G-B.; Guo, Y-L.; Dai, L-X. Tetrahedron Lett. 1993, 34, 8513.
Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Springer-Verlag, Berlin, 1978.
Hawkeswood, S.; Stephan, D.W. Dalton Trans. 2005, 2182.
Grünefeld, J.; Kliegel, W.; Rettig, S.J.; Trotter, J. Can. J. Chem. 1999, 77, 439.
Kliegel, W.; Metge, J.; Rettig, S.J.; Trotter, J. Can. J. Chem. 1997, 75, 1203.
Wolf, W.M. Acta Crystallogr. B 2001, 57, 54.
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.
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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
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DOI: https://doi.org/10.1007/s10870-006-9114-4