N.G. Khaligh, F. shirini / Ultrasonics Sonochemistry 20 (2013) 19–25
25
[
[
25] I. Scriabire, Bull. Soc. Chim. Fr. (1961) 1194.
26] (a) B.M. Trost, C.B. Lee, J.M. Weiss, J. Am. Chem. Soc. 117 (1995) 7247;
b) C.D. Wang, M.H. Li, Synth. Commun. 32 (2002) 3469.
4
. Conclusions
(
It may be reasonably concluded that the present procedure for
[27] (a) T.S. Jin, G.Y. Du, T.S. Li, Indian J. Chem. Sect. B 37 (1998) 939;
(b) X.Y. Zhang, L.J. Li, G.S. Zhang, Green Chem. 5 (2003) 546.
[
[
[
the protection of aldehydes with acetic anhydride establishes the
potential of PVPHS as a solid acid catalyst under normal reaction
conditions/ultrasonic irradiation for such the reactions and gives
hope for further useful applications in organic synthesis. Moreover,
this methodology offers substantial advantages with respect to
simplicity of operation, yield of products, reaction times, availabil-
ity of catalyst, easy work-up procedure under mild reaction condi-
tions. These significant features are expected to contribute to the
28] J.K. Michie, J.A. Miller, Synthesis (1981) 824.
29] J.S. Yadav, B.V.S. Reddy, C. Srinivas, Synth. Commun. 32 (2002) 1175.
30] L. Yin, Z.-H. Zhang, Y.-M. Wang, M.-L. Pang, Synlett (2004) 1727.
[31] B.F. Mirjalili, M.A. Zolfigol, A. Bamoniric, N. Sheikhan, J. Chin. Chem. Soc. 53
2006) 955.
32] M.M. Heravi, K. Bakhtiari, T. Benmorad, H.A. Oskooie, J. Chin. Chem. Soc. 54
2007) 273.
[33] B.P. Bandgar, N.S. Joshi, V.T. Kamble, J. Chin. Chem. Soc. 54 (2007) 489.
(
[
(
[
[
[
34] V.K. Aggarwal, S. Fonquerna, G.P. Vennall, Synlett (1998) 849.
35] K.L. Chandra, P. Saravanan, V.K. Singh, Synlett (2000) 359.
36] M.D. Carrigan, K.J. Eash, M.C. Oswald, R.S. Mohan, Tetrahedron Lett. 42 (2001)
8133.
37] B. Karimi, J. Maleki, J. Org. Chem. 68 (2003) 4951.
38] R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, J. Mol. Catal. A: Chem. 215 (2004)
development of
aldehydes.
a green strategy for the 1,1-diacylation of
[
[
Acknowledgments
49.
[
39] (a) M.V. Joshi, C.S. Narasimhan, J. Catal 141 (1993) 308;
(
(
(
b) D. Karmakar, D. Prajapati, J.S. Sandhu, J. Chem. Res. Synop. (1998) 382;
c) Z.H. Zhang, T.S. Li, C.G. Fu, J. Chem. Res. Synop. (1997) 174;
d) T.S. Li, Z.H. Zhang, Y.J. Gao, Synth. Commun. 28 (1998) 4665.
The authors are thankful to the Guilan University Research
Council for partial support of this work.
[
40] T.S. Jin, Y.R. Ma, Z.H. Zhang, T.S. Li, Synth. Commun. 27 (1997) 3379.
References
[41] (a) P. Kumar, V.R. Hedge, T.P. Kumar, Tetrahedron Lett. 36 (1995) 601;
b) C. Pereira, B. Gigante, M.J. Marcelocurto, H. Carreyre, G. Perot, M. Guisnet,
Synthesis (1995) 1077;
(
[
[
1] (a) S.C. Stinson, Chem. Eng. 74 (1996) 39;
b) K. Tanaka, F. Toka, Chem. Rev. 100 (2000) 1025.
2] (a) A.J. Fatiadi, Synthesis 1987, 85.;
(
(
c) R. Ballini, M. Bordoni, G. Bosica, R. Maggi, G. Sartori, Tetrahedron Lett. 39
1998) 7587.
(
[
[
[
[
[
42] B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett (2000) 623.
43] S.C. Roy, B. Banerjee, Synlett (2002) 1677.
44] T.S. Jin, G. Sun, Y.W. Li, T.S. Li, Green Chem. 4 (2002) 255.
45] B. Karimi, G.R. Ebrahimian, H. Seradj, Synth. Commun. 32 (2002) 669.
46] H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Tetrahedron Lett. 44 (2003)
(
(
b) F.M. Menger, C. Lee, J. Org. Chem. 44 (1979) 3446–3448;
c) K. Smith, Solid Supports and Catalysis in Organic Synthesis, Ellis Horwood
and PTR Prentice Hall, New York, 1992;
d) P. Laszlo, Comprehensive Organic Synthesis, vol. 7. Trost, B.M. (Ed.),
(
Pergamon, New York, (1991) pp. 839.
3
951.
47] G.P. Romanelli, H.J. Thomas, G.T. Baronetti, J.C. Autino, Tetrahedron Lett. 44
2003) 1301.
48] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Nocchetti, Tetrahedron Lett.
3 (2002) 2709.
[
[
[
3] D. Choudhary, S. Paul, R. Gupta, J.H. Clark, Green Chem. 8 (2006) 479.
4] A. Ghorbani-Choghamarani, S. Sardari, J. Sulfur Chem. 32 (2011) 63.
5] R. Dalpozzo, G. Bartoli, L. Sambri, P. Melchiorre, Chem. Rev. 110 (6) (2010)
[
[
(
3
501.
6] A.K. Chakraborti, B. Singh, S.V. Chankeshwara, A.R. Patel, J. Org. Chem. 74 (16)
2009) 5967.
4
[
[
[
49] G. Smitha, C.S. Reddy, Tetrahedron 59 (2003) 9571.
50] N. Sumida, K. Nishioka, T. Sato, Synlett (2001) 1921;
(
[
[
[
7] G. Sharma, R. Kumar, A.K. Chakraborti, Tetrahedron Lett. 49 (2008) 4272.
8] B. Karimi, M. Khalkhali, J. Mol. Catal. A: Chem. 232 (2005) 113.
9] K. Niknam, D. Saberi, M. Nouri Sefat, Tetrahedron Lett. 50 (2009) 4058.
(
b) J.S. Yadav, B.V.S. Reddy, C. Venugopal, T. Ramalingam, Synlett (2002) 604.
51] H.M.S. Kumar, B.V.S. Reddy, P.T. Reddy, J.S. Yadav, J. Chem. Res. Synop. (2000)
6.
[
8
[
[
[
10] K. Tanabe, W.F. Hölderich, Appl. Catal. A 181 (1999) 399.
11] J.A. Melero, R. van Grieken, G. Morales, Chem. Rev. 106 (2006) 3790.
12] (a) A. Akelah, D.C. Sherindton, Chem. Rev. 81 (1981) 557;
[
[
[
52] B.C. Rana, J. Dutta, A. Das, Chem. Lett. 32 (2003) 366.
53] A.K. Chakraborti, R. Thilagavathi, R. Kumar, Synthesis (2004) 831.
54] D.H. Aggen, J.N. Arnold, P.D. Hayes, N.J. Smoter, R.S. Mohan, Tetrahedron Lett.
(
b) D.C. Sherington, P. Hodge, Synthesis and Separation Using Functional
Polymers, Wiley, Chichester, 1988;
c) K. Takemoto, Y. Inaki, R.M. Ottenbrite, Functional Monomers and Polymers,
Dekker, New York, 1987;
d) S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A.
60 (2004) 3675.
[
[
55] A. Ziyaei, N. Azizi, M.R. Saidi, J. Mol. Catal. A: Chem. 238 (2005) 138.
56] G.E. Negron, L.N. Palacios, D. Angeles, L. Lomas, R. Gavino, J. Braz. Chem. Soc. 16
(
(
3A) (2005) 490.
57] (a) CAN/SiO : P. Ctelle, J.P. Catteau, Tetrahedron Lett. 33 (1992) 3855;
b) AlCl :I. Mohammampoor-Baltork, H. Aliyan, J. Chem. Res. Synop. (1999)
72;
c) BiCl
741;
d) SnCl
8 (1999) 1223;
(
[
2
Longbottom, M. Nesi, J.S. Scott, R.I. Storer, S.J. Taylor, J. Chem. Soc. Perkin
Trans. 1 (2000) 3815.
(
2
(
2
(
3
3
[
[
13] V. Rao, P.V. Ashokan, M.H. Shridhar, Mat. Sci. Eng. A 276 (2000) 266.
14] (a) T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, third
ed., John Wiley and Sons, New York, 1999;
3
:I. Mohammampoor-Baltork, H. Aliyan, Synth. Commun. 29 (1999)
2
Á2H
2
O:I. Mohammampoor-Baltork, H. Aliyan, Indian J. Chem. Sect. B
(
b) M.J. Gregory, J. Chem. Soc. B (1970) 1201.
15] F.R. Heerden, J.J. Huyser, D.B.G. Williams, C.W. Holzapfer, Tetrahedron Lett. 39
1998) 5281.
[
(
(
(
(
(
e) NH
f) FeCl
2
SO H:T.S. Jin, G. Sun, Y.W. Li, T.S. Li, J. Chem. Res. Synop. (2003) 30;
3
(
3
Á6H O:H.Y. Niu, X.Y. Zhang, H.M. Guo, J.J. Wang, J. Chem. Res. Synop.
2
[
[
[
16] B.M. Trost, C. Lee, J. Am. Chem. Soc. 123 (2001) 12191.
2004) 764;
g) InBr :Z.H. Zhang, L. Yin, Y. Li, Y.M. Wang, Tetrahedron Lett. 46 (2005) 889;
h) H O:G.P. Romanelli, J.C. Autino, G. Baronetti, H.J. Thomas,
17] M. Sandberg, L.K. Sydnes, Tetrahedron Lett. 39 (1998) 6361.
18] K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha, H.W. Pinnick,
Protecting groups in organic synthesis. Part 8. Conversion of aldehydes into
3
6
P
W
2 18
O
62Á24H
2
Synth. Commun. 34 (2004) 3909.
1
,1-diacetates, J. Org. Chem. 48 (1983) 1765.
[
[
58] T.J. Mason, J.P. Lorimer, In Sonochemistry: Theory, Application and Uses of
Ultrasound in Chemistry, John Wiley and Sons, New York, 1988.
59] K.S. Suslick, Ultrasound: It’s Chemical, Physical and Biological Effects, VCH,
Weinheim, 1988.
[
[
19] (a) M. Tomita, T. Kikuchi, K. Bessho, T. Hori, Y. Inubushi, Chem. Pharm. Bull. 11
(
(
1963) 1484;
b) R. Wegscheider, E. Spath, Monatsh. Chem. 30 (1909) 825.
20] (a) W. Davey, J.R. Gwilt, J. Chem. Soc. 1008 (1957);
b) F. Freeman, E.M. Karchetski, J. Chem. Eng. Data 22 (1977) 355.
[
[
[
[
[
[
60] A. Gaplovsky, M. Gaplovsky, S. Toma, J. Luche, J. Org. Chem. 65 (2000) 8444.
61] R.R. Deshmukh, R. Rajagopal, K.V. Srinivasan, Chem. Commun. (2001) 1544.
62] F. Shirini, N.G. Khaligh, Phosphorus Sulfur Silicon Relat. Elem. 186 (2011) 2156.
63] N.G. Khaligh, J. Mol. Catal. A: Chem. 349 (2011) 63.
64] N.G. Khaligh, F. Shirini, J. Mol. Catal. A: Chem. 348 (2011) 20.
65] V. Calvino-Casilda, A.J. López-Peinado, R.M. Martín-Aranda, S. Ferrera-
Escudero, C.J. Durán-Valle, Carbon 42 (2004) 1363.
(
[
[
21] J.A. Marshall, P.G.M. Wuts, J. Org. Chem. 42 (1977) 1794.
22] (a) G.A. Olah, A.K. Mehrotra, Synthesis (1982) 962;
(
(
(
b) T.S. Jin, G.Y. Du, Z.H. Zhang, T.S. Li, Synth. Commun. 27 (1997) 261;
c) T.S. Li, Z.H. Zhang, C.G. Fu, Tetrahedron Lett. 38 (1997) 3285;
d) B.M. Reddy, P.M. Sreekanth, A. Kahn, Synth. Commun. 34 (2004) 839.
[
[
23] (a) N. Deka, D.J. Kalita, R. Borah, J.C. Sarma, J. Org. Chem. 62 (1997) 563;
b) J.M. Thomas, Angew. Chem. Int. Ed. Engl. 27 (1998) 1673.
24] N. Daka, R. Borah, D.J. Kalita, J.C. Sarma, J. Chem. Res. Synop. (1998) 94.
[
66] T.J. Mason, J.P. Lorimer, B.P. Mistry, Tetrahedron 41 (1985) 5201.
(