 
(Before assuming Chair position) |
A. L. Baumstark Professor, Organic Chemistry International Editorial Board for Heterocyclic Communications 2003-present Ph.D., Harvard University, (1974) Dr. A. Baumstark Department of Chemistry Georgia State University P.O. Box 4098 Atlanta, Georgia 30302-4098
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Research in my group centers on the chemistry of oxygen-containing compounds with an emphasis on that of organic peroxides. Currently, we are focused on the mechanisms of oxygen-atom transfer reactions of unusual hydroperoxides and peroxides, especially under mild conditions. We are carrying out extensive mechanistic investigations on epoxidation, N-oxidation and CH abstraction reactions of dimethyldioxirane. We have extended the frontiers in oxygen chemistry by synthesis and characterization of exotic, novel organic peroxides. Historically we have made substantial contributions in the area of synthesized and thermolysis of 4-membered cyclic peroxides, dioxetanes. The ultimate goal of our investigations is to understand the limiting factors that control reactivity and selectivity in oxygen-containing systems.
We have developed the chemistry of cyclic and acyclic alpha-azo hydroperoxides and 3-hydroperoxy-1,2-dioxolanes. These unusual hydroperoxides are of high reactivity and selectivity in electrophilic oxygen-atom transfer reactions. We have discovered new synthetic routes to these reactive compounds. Our work on the synthesis and thermolysis of 1,2-dioxetanes has been extremely productive. We have studied the effects of substituents on the activation parameters for thermolysis. In addition, we have measured the chemiexcitation yields for a large number of compounds. Our studies have provided insights into the mechanism of excited state formation in chemiluminescent and bioluminescent processes.
We have developed 17O NMR spectroscopy methods for the investigation of structure in oxygen-containing compounds. 17O NMR studies have been successful in predicting: (a) torsion angle relationships; (b) in-plane van der Waals repulsions; and (c) hydrogen-bonding phenomena. The results of our studies have also been useful in applying 17O NMR methods to labeling studies. We are actively investigating the oxygen-atom transfer chemistry of dioxiranes, 3-membered cyclic peroxides. Our research on electrophilic epoxidation has led to postulation of a mechanism with a spiro transition state. Current investigations center on epoxidation of electron-poor systems, computational modeling of epoxidation, and heteroatom oxidation. We are also studying CH abstraction by dimethyldioxirane especially for oxidation of secondary alcohols and ethers. Mechanistically, this feature of dioxirane chemistry is highly controversial. Currently, dioxirane research is a major focus of our current research efforts.
Research lab supervised by Dr. Pedro Vasquez: phone: 404-651-3858; e-mail: chepcv@langate.gsu.edu
| Name | Position | Comments |
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| *Dr. Luiz Catalani | Associate Professor Chemistry Institute University of Sao Paulo Sao Paulo, Brazil |
Ph.D. awarded in Brazil. Did most of Ph.D. work at GSU. First Brazilian student allowed to do this; now expected by Brazilian government. |
| Dr. Hsin-Hung Chen | Postdoctoral Associate Baylor College of Medicine Houston, Texas |
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| Dr. Brian Crow | Senior Scientist Metametrix Norcross, Georgia |
Working in industry. |
| *Dr. Mark Cunningham | Assistant Professor Department of Chemistry Berea College Berea, Kentucky |
Recently moved from faculty position at Atlanta Metro (junior college) |
| *Dr. Denise Curi | Professor Department of Chemistry Colegio Bandeirantes Sao Paulo, Brazil |
Ph.D. awarded in Brazil. Did most of Ph.D. work at GSU. |
| *Dr. Pamela Leggett-Robinson | Assistant Professor Department of Chemistry Tuskeegee University Tuskeegee, Alabama |
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| *Dr. Elba Michelena-Baez | Professor Department of Chemistry Universidad del Zulia Maracaibo, Venezuela |
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| *Dr. Angela Navarro-Eisenstein | Visiting Lecturer Department of Chemistry Georgia State University Atlanta, Georgia |
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| Dr. Bob Pilcher | Orthopedic Surgeon Albany Arthritis & Orthopedic Center Albany Georgia |
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| Dr. W. Rucks Winkeljohn | Postdoctoral Associate Department of Chemistry Georgia State University Atlanta, Georgia |
Applying for faculty positions at 4-year schools. |
| *Out of ten Ph.D. students from Baumstark lab, six currently hold faculty positions and one is currently applying for a faculty position. | ||
Current Student Project Titles:
- Janet Jones, Ph.D. graduate student (joint with Professor Wang).
Project: Dioxirane Oxidations of Selected Systems Applicable to Carbohydrate Synthesis
- Joint research project with Professor Pamela Leggett-Robinson of Tuskegee University.
Project: Oxidation of Sterically Hindered Pyradines by Dimethyldioxirane
Representative Publications
"N-Oxidation of 2-Substituted Pyridines and Quinolines by Dimethyldioxirane: Kinetics and Steric Effects," W.R. Winkeljohn, P. Leggett-Robinso, M.R. Peets, L. Strekowski, P.C. Vasquez and A.L. Baumstark, Heterocyclic Commun. 2007, in press
"Epoxidation of Substituted cis/trans-1,2-Dialkylalkenes by Dimethyldioxirane: Activation Parameters," B.S. Crow, W.R. Winkeljohn, A. Navarro-Eisensterin, E. Michelena-Baez, P.J. Franklin, P.C. Vasquez and A.L. Baumstark, E. J. Org. Chem. 2006, 20, 4642.
"Synthesis of 3,3,4,4,5-Pentasubstituted-5-Vinyl-4,5-Dihydro-3H-Pyrazoles: Route to Vinylcyclopropanes," K.K. Towns, P.C. Vasquez, G.D. Kennedy and A.L. Baumstark, Heterocyclic Commun. 2006, 12, 337.
"17O NMR Spectroscopy of Heterocycles: Substituent Effects in 3,5-Diarylisoxazoles and 3,5-Diarylisoxazolines," T. Yuzuri, S. Chandrasekaran, P.C. Vasquez and A.L. Baumstark, Heterocyclic Commun. 2006, 12, 7.
"Thermolysis of trans-3-Chloro-4,4,5-Trimethyl-3,5-Diphenyl-4,5-Dihydro-3H-Pyrazole," N. Desalegn, P.C. Vasquez, P.J. Franklin, G.D. Kennedy and A.L. Baumstark, Heterocyclic Commun. 2005 11, 375.
"Chiral Discrimination in Binding of Enantiomers of 2-(Aminoalkoxy)-substituted 4-(2-Thienyl)pyrimidines and 4,6-bis(2-Thienyl)pyrimidines with Duplex DNA," L. Strekowski , M.T. Cegla, V. Honkan, H. Buczak, W.R. Winkeljohn, A.L. Baumstark, and W.D. Wilson, Bioorg Med Chem Lett. 2005, 11, 2720.
"Oxidation of Substituted Pyridines by Dimethyldioxirane: Kinetics and Solvent Effects," W.R. Winkeljohn, P.C. Vasquez, L. Strekowski and A.L. Baumstark, Tetrahedron Lett., 2004, 45, 8295.
"Epoxidation of Geraniol and Model Systems by Dimethyldioxirane: Kinetics," A.L.Baumstark, P.J. Franklin, P.C. Vasquez and B.S. Crow, Molecules, 2004, 117, 117.
Honors, Awards, etc.
- Junior Faculty Teaching Award, College of Arts and Sciences, GSU, 1982
- Camille and Henry Dreyfus Teacher-Scholar Award (1981-86)
- Golden Key National Honor Society, GSU Distinguished Research Award (1987-88)
- Advances in Oxygenated Processes, Alfons L. Baumstark, Series Editor, JAI Press Inc. Greenwich, Connecticut; 1988 - 1996.
- Editorial Board - Heterocyclic Communications, 2003-present.