Abstract
Oxovanadium(IV) complex of a Schiff base ligand derived from 2,4-dihydroxyacetophenone and 2,2′-dimethylpropanediamine has been encapsulated in the nanopores of zeolite-Y by flexible ligand method and characterized by metal analysis, IR spectroscopic studies and X-ray diffraction patterns. The encapsulated complex [VOL-Y] catalyzes the oxidation of various olefins and methyl phenyl sulfide using hydrogen peroxide as a green oxidant in good yield. Under the optimized reaction conditions, in the presence of VOL-Y, 86 % conversion of cyclooctene with 100 % selectivity for epoxide and 51 % conversion for methyl phenyl sulfide with 92 % selectivity for sulfone were obtained.
Similar content being viewed by others
References
M. Almeida, H. Humanes, R. Melo, J.A. Silva, J.J.R. Frausto de Silva, H. Vilter, R. Wever, Phytochemistry 48, 229 (1998)
H. Vilter, Bot. Mar. 26, 451 (1983)
H. Vilter, Phytochemistry 23, 1387 (1984)
P.M. Geschwend, J.K. MacFarlane, K.A. Newman, Science 227, 1033 (1985)
G.W. Gribble, Chem. Soc. Rev. 28, 335 (1999)
A. Butler, Coord. Chem. Rev. 187, 17 (1999)
G.J. Colpas, B.J. Hamstra, J.W. Kampf, V.L. Pecoraro, J. Am. Chem. Soc. 118, 3469 (1996)
G.Y. Yeh, D.M. Eisenberg, T.J. Kaptchuk, R.S. Phillips, Diabetes Care 26, 1277 (2003)
K.H. Thompson, J.H. McNeill, C. Orvig, Chem. Rev. 99(9), 2561 (1999)
G.R. Wilsky, A.B. Goldfine, P.J. Kostyniak, J.H. McNeill, L.Q.H. Yang, R. Khan, D.C. Crans, J. Inorg. Biochem. 85, 33 (2001)
L. Canali, D.C. Sherrington, Chem. Soc. Rev. 28, 85 (1999)
D.C. Sherrington, Catal. Today 57, 87 (2000)
S. Rayati, S. Zakavi, P. Jafarzadeh, O. Sadeghi, M.M. Amini, J. Porph. Phthal. 16, 260 (2012)
A. Molinari, A. Maldotti, A. Bratovcic, G. Magnacca, Catal. Today 161, 64 (2011)
A.A. Costa, G.F. Ghesti, J.L. de Macedo, V.S. Braga, M.M. Santos, J.A. Dias, S.C.L. Dias, J. Mol. Catal. A Chem. 282, 149 (2008)
K. Machado, P.B. Tavares, C. Freire, G.S. Mishra, Polyhedron 69, 119 (2014)
S. Alavi, H. Hosseini-Monfared, M. Siczek, J. Mol. Catal. A Chem. 377, 16 (2013)
S. Samadi, S. Nazari, H. Arvinnezhad, K. Jadidi, B. Notash, Tetrahedron 69, 6679 (2013)
M. Lashanizadegan, S. Rayati, Z.D. Derakhshan, Chin. J. Chem. 29, 2439 (2011)
M.R. Maurya, A.K. Chandrakar, S. Chand, J. Mol. Catal. A Chem. 263, 227 (2007)
V.K. Bansal, P.P. Thankachan, R. Prasad, Appl. Catal. A Gen. 381, 8 (2010)
C.L. Padró, E.A. Rey, L.F. González Peña, C.R. Apesteguía, Microporous Mesoporous Mater. 143, 236 (2011)
I. Craciun, M.-F. Reyniers, G.B. Marin, J. Catal. 294, 136 (2012)
B.O. Dalla Costa, C.A. Querini, Appl. Catal. A Gen. 385, 144 (2010)
Y. Ren, W. Ma, Y. Che, X. Hu, X. Zhang, X. Qian, D.M. Birney, J. Photochem. Photobiol. A Chem. 266, 22 (2013)
A. Syamal, K.S. Kale, Indian J. Chem. 19A, 225 (1980)
A.O. Chong, K.B.J. Sharplessm, Org. Chem. 42, 1587 (1977)
Y. Nishida, K. Yamada, Inorg. Chem. Acta 174, 1 (1990)
E.P. Talsi, V.D. Chinakov, V.P. Babenko, K.I. Zamaraev, J. Mol. Catal. 81, 235 (1993)
R.A. Sheldon, J.K. Kochi, Metal-catalyzed oxidation of organic compounds (Academic Press, New York, 1981). (34)
Acknowledgments
This work has been supported by the Iran National Science Foundation (INSF) (Grant No. 88001216).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rayati, S., Salehi, F. Green oxidation of olefins and methyl phenyl sulfide with hydrogen peroxide catalyzed by an oxovanadium(IV) Schiff base complex encapsulated in the nanopores of zeolite-Y. J IRAN CHEM SOC 12, 309–315 (2015). https://doi.org/10.1007/s13738-014-0485-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-014-0485-8