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Regioselective Ring-Opening of Epoxides with Thiophenols in Presence of b-Cyclodextrin in Water
Corresponding Author(s) : Siping Tang
Asian Journal of Chemistry,
Vol. 29 No. 2 (2017): Vol 29 Issue 2
Abstract
This paper reports a simple, mild and convenient method to synthesize b-hydroxysulfides. These b-hydroxysulfides were achieved with excellent yields (> 80 %) and high regioselectivity by ring-opening reaction of oxiranes with thiophenols in presence of the b-cyclodextrin at 30 °C in water. b-Cyclodextrin as catalyst greatly accelerated the reactions and can be recovered.
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- K.A. Connors, Chem. Rev., 97, 1325 (1997).
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- F. Viola, G. Balliano, P. Milla, L. Cattel, F. Rocco and M. Ceruti, Bioorg. Med. Chem., 8, 223 (2000).
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- R.-H. Fan and X.-L. Hou, J. Org. Chem., 68, 726 (2003).
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- V. Pironti and S. Colonna, Green Chem., 7, 43 (2005).
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References
K.A. Connors, Chem. Rev., 97, 1325 (1997).
J. Szejtli, Chem. Rev., 98, 1743 (1998).
G. Cravotto, A. Binello, E. Baranelli, P. Carraro and F. Trotta, Curr. Nutr. Food Sci., 2, 343 (2006).
A.R. Hedges and C. McBride, Cereal Foods World, 44, 700 (1999).
D.R. Alston, P.R. Ashton, T.H. Lilley, J. Fraser Stoddart, R. Zarzycki, A.M.Z. Slawin and D.J. Williams, Carbohydr. Res., 192, 259 (1989).
N.S. Krishnaveni, K. Surendra, M.A. Reddy, Y.V.D. Nageswar and K.R. Rao, J. Org. Chem., 68, 2018 (2003).
D.P. Shi and H.B. Ji, Chin. Chem. Lett., 20, 139 (2009).
B. Srinivas, V.P. Kumar, R. Sridhar, K. Surendra, Y.V.D. Nageswar and K.R. Rao, J. Mol. Catal. A, 261, 1 (2007).
B. Srinivas, R. Sridhar, K. Surendra, N.S. Krishnaveni, V.P. Kumar, Y.V.D. Nageswar and K.R. Rao, Synth. Commun., 36, 3455 (2006).
M.S. Reddy, M. Narender, Y.V.D. Nageswar and K.R. Rao, Tetrahedron Lett., 46, 6437 (2005).
F. Viola, G. Balliano, P. Milla, L. Cattel, F. Rocco and M. Ceruti, Bioorg. Med. Chem., 8, 223 (2000).
A. Conchillo, F. Camps and A. Messeguer, J. Org. Chem., 55, 1728 (1990).
I.A. Dotsenko, M. Curtis, N.M. Samoshina and V.V. Samoshin, Tetrahedron, 67, 7470 (2011).
S. Hammarström, B. Samuelsson, D.A. Clark, G. Goto, A. Marfat, C. Mioskowski and E.J. Corey, Biochem. Biophys. Res. Commun., 92, 946 (1980).
J.R. Luly, N. Yi, J. Soderquist, H. Stein, J. Cohen, T.J. Perun and J.J. Plattner, J. Med. Chem., 30, 1609 (1987).
E.J. Corey, D.A. Clark, A. Marfat and G. Goto, Tetrahedron Lett., 21, 3143 (1980).
A.K. Shivani and A.K. Chakraborti, J. Mol. Catal. Chem., 263, 137 (2007).
J. Cossy, V.R. Bellosta, C. Hamoir and J.-R. Desmurs, Tetrahedron Lett., 43, 7083 (2002).
F. Fringuelli, F. Pizzo, S. Tortoioli and L. Vaccaro, Tetrahedron Lett., 44, 6785 (2003).
V. Polshettiwar and M.P. Kaushik, Catal. Commun., 5, 515 (2004).
J. Sun, F. Yuan, M. Yang, Y. Pan and C. Zhu, Tetrahedron Lett., 50, 548 (2009).
R.-H. Fan and X.-L. Hou, J. Org. Chem., 68, 726 (2003).
M.S. Reddy, B. Srinivas, R. Sridhar, M. Narender and K.R. Rao, J. Mol. Catal. Chem., 255, 180 (2006).
V. Pironti and S. Colonna, Green Chem., 7, 43 (2005).
F. Fringuelli, F. Pizzo, S. Tortoioli and L. Vaccaro, Green Chem., 5, 436 (2003).
S.-P. Tang, Y.-H. Zhou, H.-Y. Chen, C.-Y. Zhao, Z.-W. Mao and L.-N. Ji, Chem. Asian J., 4, 1354 (2009).
H. Fu, Y.-H. Zhou, W.-L. Chen, Z.-G. Deqing, M.-L. Tong, L.-N. Ji and Z.-W. Mao, J. Am. Chem. Soc., 128, 4924 (2006).