Western Illinois University: Macomb Campus
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Dr. Thottumkara K. Vinod
The overarching goal of the current research in our laboratory is the development and optimization of various chemoselective oxidation procedures using water- soluble hypervalent iodine reagents. Underlying green chemistry themes such as the use of benign oxidants, the use of aqueous solvent mixtures as reaction media and the feasibility of carrying out the synthetically useful oxidative transformations under catalytic conditions in presence of environmentally friendly co-oxidants are highlights and worthwhile aspects of the ongoing projects. We also focus on the mechanistic aspects of these chemoselective oxidative transformations. A careful evaluation of the mechanism of oxidation of alcohols carried out using water-soluble hypervalent iodine reagents in different solvents have allowed us to map out a series of feasible and predictable chemoselective oxidations from knowledge of the C-H bond dissociation energies of the bond involved in the oxidation step. Methodologies for chemoselective oxidation of a select methyl group on heterocyclic rings, selective introduction of -unsaturation in ketones over aldehydes, introduction of -unsaturation with predictable regiochemistry in unsymmetrical ketones, potential and possible selective oxidation of aliphatic aldehydes over aromatic aldehydes are a few of the different selective oxidation methods currently under investigation.
The specific goals, nature of the experiments, the theoretical basis for the observed selectivity, and synthetic targets for the different projects are both intellectually and practically suitable for the proper training of undergraduate and MS students at Western Illinois University. We have published pedagogically relevant aspects of the ongoing research program in our laboratory as classroom activities and as useful experiments in the Journal of Chemical Education. In addition to providing undergraduate with chemical research experience our lab also takes pride in training local high school students in the art of research and some of these students have placed well at national science fair competitions including Siemens Competition, Intel Science Talent Search and Intel International Science and Engineering Fair (ISEF).
MWF 10:00-11:30, or by appointment
B.S. University of Calicut; M.S. University of Calicut; Ph. D. University of Victoria, Canada (1986); Post-Doctoral Fellow: Michigan State University (1986-1991), University of Oregon (1992-1994)
Organic Chemistry, Advanced NMR Spectroscopy
Synthesis and oxidations using water-soluble hypervalent iodine reagents, synthesis of molecular solids, green chemistry.
Research Mentor Recognition, Siemens Foundation: 2004 &2010
Research Mentor Recognition, Science Service and Intel Corporation: 2004 &2011
Current Research Funding
National Science Foundation: (CHE-0910565)
Donors of the American Chemical Society Petroleum Research Funds (50086-URI)
Versatile Iodine Atom Economic Coiodination of Alkenes, Gottam, H. B.; Vinod, T. K. J. Org. Chem. 2011,76, 974-977.
Oxidative Cleavage of Alkenes Using an In SituGenerated IodoniumIon with Oxone as a Terminal Oxidant, Thottumkara, P. P.; Vinod, T. K. Org. Lett. 2010, 12, 5640-5643.
Benzylic Carbon oxidation by In-Situ Formed o-Iodoxybenzoic Acid (IBX) Derivative, Ojha, L. R.; Kudugunti, S.; Madukkuri, P. P., Kommreddy, A.; Gunna, M.; Dokuparthy, P.; Gottam, H. B.; Botha, K. K.; Parapati, D. R.; Vinod, T. K. SynLett. 2009, 132-136.
Synthesis and Solvent Dependant Oxidation Behavior of a Water-Soluble IBX Derivative, Kommareddy, A.; Bowsher, M. S.; Botha, K.; Gunna. M.; Vinod, T. K. Tetrahedron Lett. 2008, 49, 4378-4382.
Oxidation of Aromatic Aldehydes using Oxone, Gandhari, R.; Maddukuri, P.P.; Vinod, T. K. J. Chem. Ed. 2007, 84, 852-854.
In Situ Generation of o-Iodoxybenzoic acid (IBX) and the Catalytic Use of it in Oxidation Reactions in Presence of Oxone® as a Co-Oxidant. Bowsher, M. S.; Thottumkara, A. P.; Vinod, T. K. Org. Lett, 2005, 7, 2933-2936.