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http://dx.doi.org/10.5012/bkcs.2013.34.3.820

N,N,N',N'-Tetrahalobenzene-1,3-disulfonamide/PPh3 as an Efficient System for the Preparation of Alkyl Halides  

Ghorbani-Vaghei, Ramin (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University)
Shiri, Lotfi (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University)
Ghorbani-Choghamarani, Arash (Department of Chemistry, Faculty of Sciences, Ilam University)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.3, 2013 , pp. 820-822 More about this Journal
Abstract
N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide (TBBDA)/$PPh_3$ and N,N,N',N'-tetrachlorobenzene-1,3-disulfonamide (TCBDA)/$PPh_3$ are two highly reactive reagent systems for the conversion of alcohols corresponding into alkyl chlorides and bromides in moderate to excellent yields in dichloromethane at room temperature under mild and neutral conditions.
Keywords
Alcohol; Alkyl halide; N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide (TBBDA); N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide (TCBDA); Triphenylphosphine ($PPh_3$);
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1 Vanlaer, S.; Voet, A.; Gielens, C.; De Maeyer, M.; Compernolle, F. Eur. J. Org. Chem. 2009, 643.
2 Mojumdar, S. C.; Simon, P.; Krutosikova, A. J. Therm. Anal. Calorim. 2009, 96, 103.   DOI
3 Morgentin, R.; Jung, F.; Lamorlette, M.; Maudet, M.; Menard, M.; Ple, P.; Pasquet, G.; Renaud, F. Tetrahedron 2009, 65, 757.   DOI   ScienceOn
4 Luca, L. D.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 4, 553.
5 Snyder, E. I. J. Org. Chem. 1972, 37, 1466.   DOI
6 Bringmann, G.; Schneider, S. Synthesis 1983, 139.
7 Magid, R. M.; Fruchey, O. S.; Johnson, W. L. Tetrahedron Lett. 1977, 18, 2999.   DOI   ScienceOn
8 Matveeva, E. D.; Yalovskaya, A. I.; Cherepanov, I. A.; Bundel, Y. G.; Kurts, A. L. Zh. Org. Khim. 1991, 27, 1611.
9 Pluempanupat, W.; Chavasiri, W. Tetrahedron Lett. 2006, 47, 6821.   DOI   ScienceOn
10 Hiegel, G. A.; Rubino, M. Synth. Commun. 2002, 32, 2691.   DOI   ScienceOn
11 Quallich, G. J.; Fox, D. E.; Friedmann, R. C.; Murtiashaw, C. W. J. Org. Chem. 1992, 57, 761.   DOI
12 Sato, N.; Narita, N. J. Heterocycl. Chem. 1999, 36, 783.   DOI
13 Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F. Tetrahedron Lett. 2006, 47, 1771.   DOI   ScienceOn
14 Tongkate, P.; Pluempanupat, W.; Chavasiri, W. Tetrahedron Lett. 2008, 49, 1146.   DOI   ScienceOn
15 Joseph, K. M.; Larraza-Sanchez, I. Tetrahedron Lett. 2011, 52, 13.   DOI   ScienceOn
16 Kijrungphaiboon, W.; Chantarariwong, O.; Chavasiri, W. Tetrahedron Lett. 2012, 53, 674.   DOI   ScienceOn
17 Whaley, A. M.; Copenhaver, J. E. J. Am. Chem. Soc. 1938, 60, 2497.   DOI
18 Iranpoor, N.; Firouzabadi, H.; Nowrouzi, N.; Firouzabadi, D. Tetrahedron Lett. 2006, 47, 6879.   DOI   ScienceOn
19 Ghorbani-Vaghei, R.; Akbari-Dadamahaleh, S. Tetrahedron Lett. 2009, 50, 1055.   DOI   ScienceOn
20 Ghorbani-Vaghei, R.; Khazaei, A. Tetrahedron Lett. 2003, 44, 7525.   DOI   ScienceOn
21 Ghorbani-Vaghei, R.; Zolgol, M. A.; Chegeny, M.; Veisi, H. Tetrahedron Lett. 2006, 47, 4505.   DOI   ScienceOn
22 Ghorbani-Vaghei, R.; Chegini, M.; Veisi, H.; Karimi-Tabar, M. Tetrahedron Lett. 2009, 50, 1861.   DOI   ScienceOn
23 Ghorbani-Vaghei, R.; Amiri, M.; Moshfeghifar, N.; Veisi, H.; Akbari-Dadamahaleh, S. J. Iran. Chem. Soc. 2009, 6, 754.   DOI
24 Ghorbani-Vaghei, R.; Shahbazee, E.; Veisi, H. Mendeleev. Commun. 2005, 15, 207.   DOI
25 Ghorbani- Vaghei, R.; Shahbazee, E. J. Braz. Chem. Soc. 2005, 16, 647.   DOI   ScienceOn
26 Ghorbani-Vaghei, R.; Veisi, H. Mol. Diversity 2010, 14, 249.   DOI
27 Ghorbani-Vaghei, R.; Karimi-Nami, R.; Toghraei-Semiromi, Z.; Amiri, M.; Ghavidel, M. Tetrahedron 2011, 67, 1930.   DOI   ScienceOn
28 Ghorbani- Vaghei, R.; Veisi, H.; Amiri, M. J. Iran. Chem. Soc. 2009, 6, 761.   DOI
29 Veisi, H.; Ghorbani-Vaghei, R.; Mahmoodi, J. Bull. Korean Chem. Soc. 2011, 32, 3692.   DOI   ScienceOn
30 Ghorbani-Vaghei, R.; Veisi, H. J. Braz. Chem. Soc. 2005, 21, 193.
31 Ghorbani-Vaghei, R.; Veisi, H. Synthesis 2009, 945.
32 Ghorbani-Vaghei, R.; Shahbazi, H.; Veisi, H. Tetrahedron Lett. 2012, 53, 2325.   DOI   ScienceOn
33 Ghorbani-Vaghei, R.; Jalili, H. Synthesis 2005, 1099.
34 Ghorbani-Vaghei, R.; Veisi, H.; Amiri, M. J. Chin. Chem. Soc. 2007, 54, 1257.