POLY(4-VINYLPYRIDINE)–SUPPORTED SULFURIC ACID
1385
CONCLUSION
In this report, we have successfully demonstrated the catalytic activity of
P4VP-H SO and its use as a simple, ecofriendly, reusable, and efficient heteroge-
2
4
neous acid catalyst for the chemoselective synthesis of 1,1-diacetates from aldehydes
in dichloromethane at room temperature along with deprotection reaction in
acetonitrile.
ACKNOWLEDGMENT
We are thankful to the Sophisticated Intrument Facility and Chemical Sciences
Department, Tezpur University, for analysis of various samples for this work.
REFERENCES
1
. Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-supported organic catalysts. Chem. Rev.
003, 103, 3401.
2
2
. Borah, K. J.; Dutta, P.; Borah, R. Synthesis, Characterization, and application of
poly(4-vinylpyridine)-supported Brønsted acid as reusable catalyst for acetylation reac-
tion. Bull. Korean Chem. Soc. 2011, 32, 225.
3
4
5
. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-
Interscience: New York, 1999; 306.
. Gregory, M. J. Evidence for a cyclic AA11 mechanism in the hydrolysis of benzylidene
diacetates. J. Chem. Soc. B 1970, 1201.
. Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N.; Pinnick, H. W.
Protecting groups in organic synthesis, part 8: Conversion of aldehydes into geminal dia-
cetates. J. Org. Chem. 1983, 48, 1765.
6. Frick, Jr. J. G.; Harper, R. J. Acetals as crosslinking reagents for cotton. J. Appl. Polymer
Sci. 1984, 29, 1433.
7
8
. Eanderson, W. R. Eur. Pat. Appl. EP 125,781. Chem. Abstr. 1985, 102, P64010K.
. (a) Sandberg, M.; Sydnes, L. K. The chemistry of acylals, part II: Formation of nitriles by
treatment of acylals with trimethylsilylazide in the presence of a Lewis acid. Tetrahedron
Lett. 1998, 39, 6361; (b) Sydnes, L. K.; Sandberg, M. The chemistry of acylals, part I: The
reactivity of acylals towards Grignard and organolithium reagents. Tetrahedron 1997, 53,
12679; (c) Trost, B. M.; Vercauteren, J. Allylic geminal diacetates: Unusual carbonyl sub-
stituted via metal catalyzed reactions. Tetrahedron Lett. 1985, 26, 131; (d) Trost, B. M.;
Lee, C. B.; Weiss, J. M. Asymmetric alkylation of allylic gem-dicarboxylates. J. Am.
Chem. Soc. 1995, 117, 7247.
9
. (a) Michie, J. K.; Miller, J. A. Phosphorus trichloride as catalyst in preparation of 1,1-
diacetates from aldehydes. Synthesis 1981, 824; (b) Deka, N.; Kalita, D. J.; Borah, R.;
Sarma, J. C. Iodine as acetylation catalyst in the preparation of 1,1-diacetates from
aldehydes. J. Org. Chem. 1997, 62, 1563; (c) Karimi, B.; Seradj, H.; Ebrahimian, G. R.
Mild and efficient conversion of aldehydes to 1,1-diacetates catalyzed with
N-bromosuccinimide (NBS). Synlett 2000, 623; (d) Deka, N.; Borah, R.; Kalita, D. J.;
Sarma, J. C. Synthesis of 1,1-diacetates from aldehydes using trimethylchlorosilane and
sodium iodide as catalyst. J. Chem. Res., Synop. 1998, 94.
1
0. (a) Jin, T.-S.; Du, G. Y.; Li, T.-S. An efficient and convenient procedure for the synthesis
of 1,1-diacetates of aldehydes catalysed by anhydrous ferrous sulfate. Ind. J. Chem. Sect.
B 1998, 37, 939; (b) Roy, S. C.; Banerjee, B. A mild and efficient method for the chemo-
selective synthesis of acylals from aldehydes and their deprotection catalysed by ceric