Abstract
Crosslinked polymer-supported analogue of pyrazolinium permanganate was prepared and developed as new recyclable solid-phase oxidizing reagents. The preparation of this new reagent involved a four step polymer analogous reaction starting from divinyl benzene (DVB), ethyleneglycol dimethacrylate (EGDMA), and N,N′-methylene-bis-acrylamide (N,N′MBA) crosslinked poly(methyl methacrylate) (PMMA). (N,N′MBA crosslinked reagent was found to be efficient in terms of functional group capacity, reaction time, and product yield. This reagent oxidized primary and secondary alcohols to the corresponding carbonyl compounds in high yields. The spent polymeric reagent after oxidation can be easily removed by filtration and be regenerated many times by treating with KMnO4 without loss of capacity.
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N. K. Mathur, C. K. Narang, and R. E. Williams, “Polymers as Aids in Organic Chemistry,” Academic Press, New York, N.Y., 1980.
P. Hodge and D. C. Sherrington, (Ed)., “Polymer Supported Reactions in Organic Synthesis,” Wiley, New York, N.Y., 1980.
M. A. Kranus and A. Patchornik, Macromol. Rev., 15, 55 (1980).
A. Patchornik, in “Macromolecules,” H. Benoit, P. Rempp, Ed., Pergamon Press, Oxford, 1982, p 133.
A. Akelah and D. C. Sherrington, Chem. Rev., 81, 557 (1981).
R. B. Merrifield, J. Am. Chem. Soc., 85, 2149 (1963).
V. Paulette and A. Isabella, J. Chem. Soc., Perkin Trans. 1, 66, 1351 (1984).
B. Sket, M. Zupan, and P. Zupet, Tetrahedron, 40, 1606 (1984).
J. I. Crowley and H. Rapoport, Acc. Chem. Res., 9, 135 (1976).
J. A. Grieg and D. C. Sherrington, Polymer, 19, 163 (1978).
D. P. Hart, in “Macromolecular Synthesis,” J. A. Moore, Ed., Wiley, New York, N.Y., 1977, Collect Vol. I, p 23.
S. Siggia, “Quanititative Organic Analysis via Functional Group,” 2nd ed, John Wiley and Sons Inc., New York, N.Y., 1954, p 10.
K. J. John and V. N. R. Pillai, J. Polym. Sci., Part A: Polym. Chem., 27, 2897 (1989).
K. J. John, Ph.D. Thesis, M. G. University, Kottayam, 1989.
J. Zacharias and V. N. R. Pillai, Abstracts, “National Seminar on New Frontiers in Chemistry,” Publication Division, University of Kerala, Trivandrum, 1991, p 37.
L. Fieser and M. Fieser, Advanced Organic Chemistry, 409 (1961).
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Abraham, S., Rajan, P. & Sreekumar, K. Poly(methyl methacrylate) Supported Pyrazolinium Permanganate: A New Oxidizing Reagent. Polym J 29, 12–16 (1997). https://doi.org/10.1295/polymj.29.12
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DOI: https://doi.org/10.1295/polymj.29.12