Rapid oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers with CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite

Authors

1 Department of Chemistry, College of Science, University of Guilan, Rasht, 41335, Iran

2 Department of Chemistry, College of Science, University of Guilan, Rasht, 41335, Iran.

3 Department of Chemistry, School of Sciences, Payame Noor University (PNU), Iran, 19395-3697

Abstract

A mild, efficient and fast method for the oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers to their corresponding carbonyl compounds using CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite (SANM) and under solvent-free conditions is reported. All reactions were performed at room temperature in high to excellent yields. Ease of the preparation and handling of the catalyst, heterogeneous conditions, easy work-up of the products and high reaction rates are the main advantages of this method.

Keywords


T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm (2011). J. Org. Chem.. 99, 8154-8159
E.J. Parish, S.A. Kizito, R. Heidepriem (1993). Synth. Commun. 23, 223-230
J. Muzart (1993). Synthesis. , 11-27
H. Firouzabadi, I. Mohammadpoor-Baltork (1994). Synth. Commun. 24, 1965-1077
H. Firouzabadi, F. Shirini (1996). Synth. Commun. 26, 423-432
A.R. Hajipour, M. Mostafavi, A.E. Ruoho (2007). Catal. Commun. 8, 1825-1828
G. Cainell, G. Cardillo, M. Orena, S. Sandri (1976). J. Am. Chem. Soc. 98, 6737-6738
F. Shirini, M. Esm-Hosseini, Z. Hejazi (2006). Chem. Res(S)., (2006) 29-31. , 29-31
E.P. Giannelis, R. Krishnamoorti, E. Manias (1999). Adv. Polym. Sci. 138, 107-147
F. Shirini, M. Khademian, M. Abedini (2008). ARKIVOC xv. XV, 71-78
F. Shirini, S. Saeidi (2008). Chin. Chem. Lett. 19, 676-680
F. Shirini, M. Abedini, A. Pourvali (2011). Chin. Chem. Lett., 22 (2011) 33-36.. 22, 33-36
E. Santaniello, F. Ponti, A. Manzocchi (1978). Synthesis. , 534-535
Y.S. Cheng, W.L. Liu, S.H. Chen (1980). Synthesis. , 223-224
J.M. Aizpuruan, C. Palomo (1983). Tetrahedron Lett. 24, 4367-4370
J.D. Lou, Y.Y. Wu (1987). Synth. Commun. 17, 1717-1720
J.D. Lou (1989). Synth. Commun. 19, 1841-1845
H. Nakamura, H. Matsuhashi (1995). Bull. Chem. Soc. Jpn. 68, 997-1000
M.M. Heravi, D. Ajami, K. TabarHydar, M. Ghassemzadeh (1999). J. Chem. Res. , 334-335
L.H. Huang, J.D. Lou, L.H. Zhu, L. Ping, Y.B. Fu (2005). Molecules. , 794-799
A.R. Kiasat, F. Kazemi, K. Nourbakhsh (2005). Indian J. Chem. 44B, 1524-1526
G. Zhou, Z. Zhang, X. Feng, B. Dang, X. Li, Y. Sun (2012). Catal. Commun. 25, 69-73
H. Firouzabadi, F. Shirini (1996). Synth. Commun.. 26, 649-655
A.R. Hajipour, S.E. Mallakpour, I. Mohammadpoor-Baltork, M. Malakoutikhah (2002). Tetrahedron. 58, 143-146
M. Tajbakhsh, M.M. Lakouraj, A. Fadavi (2004). Synth. Commun. 34, 1173-1182
P. Karthikeyan, S. Arunrao Aswar, P. Narayan Muskawar, P. Rambhau Bhagat, S.S. Kumar (2012). Catal. Commun. 26, 189-193
X. Huang, X. Wang, M. Tan, X. Zou, W. Ding, X. Lu (2013). Appl. Catal. A: General. 467, 407-413
H. Atashin, R. Malakooti (2013). J. Saudi Chem. Soc.
M.M. Hashemi, Y. Ahmadibeni, (2003). Monatsh. Chem. 134, 411-418
H. Anderson, H. Uh (1973). Synth. Commun. 3, 115-123
H. Zhao, L. Zeng, Y. Li, C. Liu, B. Hou, D. Wub, N. Feng, A. Zheng, X. Xie, S. Su, N. Yu (2013). Micropor. Mesopor. Mat. 172, 67-76
J.M. Lalancette, G. Rollin, P. Dumas (1972). Can. J. Chem. 50, 3058-3062
S. Filippo, C.I. Chern (1977). J. Org. Chem. 42, 2182-2183
A.S. Burange, R.V. Jayaram, R. Shukla, A.K. Tyagi (2013). Catal. Commun. 40, 27-31
C.M. Granadeiro, P. Silva, V.K. Saini, F.A. Almeida Paz, J. Pires, L.Cunha-Silva, S.S. Balula (2013). Catal. Today. 218-219, 35-42
F. Bergaya, G. Lagaly (2001). Appl. Clay. Sci. 19, 1-3
R.S. Varma, R. K. Saini (1998). Tetrahedron Lett., 39 (1998) 1481-1482.. 39, 1481-1482
F. Shirini, M. Mamaghani, S.V. Atghia (2011). Catal. Commun. 12, 1088-1094
A.R. Pourali, M. Tabaean, S.M.R. Nazifi (2012). Chin. Chem. Lett. 23, 21-24
P. Sadeghzadeh (2011). P. Sadeghzadeh, Ms.C. Thesis, University of Guilan.
F. Shirini, M. A. Zolfigol, S. Torabi (2006). Synth. Commun., 36 (2006) 2833-2840.. 36, 2833-2840
F. Shirini, M. R. Yazdanbakhsh, M. Mahdavi Pop-Kiadeh, M. Abedini (2008). J. Chem. Res(S). , 409-419
F. Shirini, M. A. Zolfigol, M. Abedini (2008). Scientia Iranica. 15, 440-443
F. Shirini, M.A. Zolfigol, M. Khaleghi (2003). Bull. Korean Chem. Soc. 24, 1021-1022