Beilstein Journal of Organic Chemistry 2009, 5, No. 75.
11.Ryu, I.; Matsubara, H.; Nakamura, H.; Curran, D. P.
Solvent-free PV-PTFE reaction design is simple and inex-
pensive. With this experimental set up, reactions involving
iodine monochloride worked well and we were able to avoid
problems associated with a solid product coating PTFE tape.
Bromine needed to be measured only if the stoichiometry was
important (4-bromophenol) and was desirable when formation
of byproducts was possible (2,4-dibromophenol). Usually, the
end point of a reaction can be determined by color of bromine
vapors persisting and the tube with unused bromine can be
stored for future use. Alternatively, the end point was deter-
mined by replacing the delivery tube with a stopper and
weighing the reaction flask taking into account the weight of
bromine vapors. This reaction design avoids use of solvents and
generates little or no waste while providing the reaction
products in high yield and in high purity.
trans-1,2-Dibromocyclohexane. The Phase Vanishing Bromination with
FC-72 as a Screen Phase. In Handbook of Fluorous Chemistry;
Gladysz, J. A.; Curran, D. P.; Horvath, I. T., Eds.; Wiley-VCH Verlag
GmbH & Co. KGaA: Weinheim, Germany, 2004; pp 468–470.
12.Matsubara, H.; Tsukida, M.; Yasuda, S.; Ryu, I. J. Fluorine Chem.
13.Ma, K.; Li, S.; Weiss, R. G. Org. Lett. 2008, 10, 4155–4158.
14.Ma, K.; Li, S.; Weiss, R. G. Org. Lett. 2009, 11, 1461.
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16.Windmon, N.; Dragojlovic, V. Tetrahedron Lett. 2008, 49, 6543–6546.
17.3M Fluorinert Electronic Liquid FC-72 Product Information.
(accessed on Mar 23, 2009).
18.Chu, Q.; Yu, M. S.; Curran, D. P. Tetrahedron 2007, 63, 9890–9895.
Supporting Information
19.Ryu, I.; Matsubara, H.; Nakamura, H.; Curran, D. P. Chem. Rec. 2008,
Supporting Information File 1
Additional experimental details and 1H NMR spectra of the
isolated dibromostilbenes (10 and 12).
20.Dinh, L. V.; Gladysz, J. A. Angew. Chem., Int. Ed. 2005, 44,
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Acknowledgments
24.Ruasse, M.-F.; Dubois, J.-E. J. Org. Chem. 1974, 39, 2441–2444.
We thank Salvatore Lepore, Department of Chemistry, Florida
Atlantic University, for use of his facilities and helpful discus-
sions and Deboprosad Mondal, Department of Chemistry,
Florida Atlantic University, for recording NMR spectra. Finan-
cial support from the Wilkes Honors College of Florida Atlantic
University is gratefully acknowledged.
25.Bellucci, G.; Chiappe, C.; Lo Moro, G. J. Org. Chem. 1997, 62,
26.Windmon, N.; Dragojlovic, V. Green Chem. Lett. Rev. 2008, 1,
License and Terms
References
1. Ryu, I.; Matsubara, H.; Yasuda, S.; Nakamura, H.; Curran, D. P.
2. Luo, Z.; Swaleh, S. M.; Theil, F.; Curran, D. P. Org. Lett. 2002, 4,
This is an Open Access article under the terms of the
Creative Commons Attribution License
permits unrestricted use, distribution, and reproduction in
any medium, provided the original work is properly cited.
3. Nakamura, H.; Usui, T.; Kuroda, H.; Ryu, I.; Matsubara, H.; Yasuda, S.;
4. Jana, N. K.; Verkade, J. G. Org. Lett. 2003, 5, 3787–3790.
The license is subject to the Beilstein Journal of Organic
Chemistry terms and conditions:
5. Curran, D. P.; Werner, S. Org. Lett. 2004, 6, 1021–1024.
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The definitive version of this article is the electronic one
which can be found at:
8. Podgoršek, A.; Stavber, S.; Zupan, M.; Iskra, J. Eur. J. Org. Chem.
9. Matsubara, H.; Yasuda, S.; Ryu, I. Synlett 2003, 247–249.
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