Selective conversion of alcohols and phenols to tetrahydropyranyl ethers catalyzed with N-chlorosaccharin under mild and solvent-free conditions

Subject Areas : Iranian Journal of Catalysis

Ghasem Aghapour ¹ (School of Chemistry, Damghan University, Damghan, 36715-364, Iran.)
Ali Kazemi Moghaddam ² (School of Chemistry, Damghan University, Damghan, 36715-364, Iran.)
Samaneh Nadali ³ (School of Chemistry, Damghan University, Damghan, 36715-364, Iran.)

Received: 2015-11-10 Accepted : 2016-08-23 Published : 2016-12-01

Keywords:

References:

[1] T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991.
[2] N. Deka, J.C. Sarma, Synth. Commun. 30 (2000) 4435-4441.
[3] B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, S.V. Patil, Monatsh. Chem. 134 (2003) 425-428.
[4] V.V. Namboodiri, R.S. Varma, Tetrahedron Lett. 43 (2002) 1143-1146.
[5] J.R. Stephens, P.L. Butler, C.H. Clow, M.C. Oswald, R.C. Smith, R.S. Mohan, Eur. J. Org. Chem. 2003 (2003) 3827-3831.
[6] Y.-G. Wang, X.-X. Wu, Z.-Y. Jiang, Tetrahedron Lett. 45 (2004) 2973-2976.
[7] Y.J. Kim, R.S. Varma, Tetrahedron Lett. 46 (2005) 1467-1469.
[8] D. M. Pore, U.V. Desai, R.B. Mane, P.P. Wadgaonkar, Synth. Commun. 34 (2004) 2135-2142.
[9] A.T. Khan, L.H. Choudhury, S. Ghosh, Tetrahedron Lett. 45 (2004) 7891-7894.
[10] A.T. Khan, T. Parvin, L.H. Choudhury, Synthesis (2006) 2497-2502.
[11] F. Shirini, M.A. Zolfigol, A.R. Abri, Chin. Chem. Lett. 18 (2007) 803-806.
[12] P.S. Poon, A.K. Banerjee, L. Bedoya, M.S. Laya, E.V. Cabrera, K.M. Albornoz, Synth. Commun. 39 (2009) 3369-3377.
[13] D.B.G. Williams, S.B. Simelane, M. Lawton, H.H. Kinfe, Tetrahedron 66 (2010) 4573-4576.
[14] A.A. Dos Santos, Jr. G.A. Brito, M.V.L. Archilha, T.G. A. Bele, G.P. Dos Santos, M.B.M. De Mello, J. Braz. Chem. Soc. 20 (2009) 42-45.
[15] N. Bodipati, S.R. Palla, R.K. Peddinti, Indian J. Chem. 51B (2012) 356-361.
[16] K. Tanemura, T. Suzuki, Tetrahedron Lett. 54 (2013) 6740-6743.
[17] S.A. Van den Berg, R.A.M. Frijns, T. Wennekes, H. Zuihof, J. Flow Chem. 5 (2015) 95-100.
[18] (a) N. Iranpoor, H. Firouzabadi, G. Aghapour, Synlett (2001) 1176-1178. (b) N. Iranpoor, H. Firouzabadi, G. Aghapour, Synth. Commun. 32 (2002) 2535-2541. (c) G. Aghapour, A. Afzali, Synth. Commun. 38 (2008) 4023-4035. (d) G. Aghapour, A. Afzali, Phosphorus Sulfur Silicon Relat. Elem. 186 (2011) 598-605. (e) G. Aghapour, A. Kazemi Moghaddam, S. Nadali, J. Chin. Chem. Soc. 62 (2015) 197-203.
[19] S.P.L. De Souza, J.F.M. Dasilva, M.C.S. De Mattos, Synth. Commun. 33 (2003) 935-939.
[20] J.H.V. Boom, J.D.M. Herschied, Synthesis (1973) 169-170.
[21] T.H. Fife, L.K. Jao, J. Am. Chem. Soc. 90 (1968) 4081-4085.