College of Arts & Sciences
A.L. Baumstark
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Al Baumstark Professor Organic Chemistry B.A. (1970): University of California, Riverside A.M. (1972) : Harvard University Ph.D. (1974) : Harvard University Postdoctoral Fellowship (1974-1976) : Harvard University Dr. Al Baumstark Department of Chemistry Georgia State University P.O. Box 4098 Atlanta, Georgia 30302-4098 Department Office Phone: 404-413-5500 Hours: M-F 9am - 5:30pm
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Research in my group centers on the chemistry of oxygen-containing compounds with an emphasis on that of organic peroxides. We have focused on the mechanisms of oxygen-atom transfer reactions of unusual hydroperoxides and peroxides, especially under mild conditions. We have extended the frontiers in oxygen chemistry by synthesis and characterization of exotic, novel organic peroxides. 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 (4-membered cyclic peroxides) was extremely productive. We have studied the effects of substituents on the activation parameters of thermolysis. We have measured the chemiexcitation yields for a large number of compounds. These studies provided insights into the mechanism of excited state formation in chemiluminescent and bioluminescent processes.
We have developed 17O NMR spectroscopic methods for the investigation of structure in oxygen-containing compounds. 17O NMR studies were successful in predicting: (a) torsion angle relationships; (b) in-plane van der Waals repulsions; and (c) hydrogen-bonding phenomena. The results of our studies were useful in applying 17O NMR methods to structural and labeling studies.
We are investigating the oxygen-atom transfer chemistry of dioxiranes, 3-membered cyclic peroxides. Our research on electrophilic epoxidation led to postulation of a mechanism with a spiro transition state, which has become the accepted explanation. Recent investigations have centered on epoxidation of electron-poor systems, computational modeling of epoxidation, and heteroatom oxidation. Currently we are studying CH abstraction by dimethyldioxirane especially for oxidation of secondary alcohols and ethers. Mechanistically, this feature of dioxirane chemistry is highly controversial.
Research lab supervised by Dr. Pedro Vasquez: phone: 404-413-5518; e-mail: chepcv@gsu.edu
| Ph.D.'s from Dr. Baumstark's Group | ||
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| Name | Position | Comments |
| *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 standard practice and expected by Brazilian government. |
| Dr. Hsin-Hung Chen | Postdoctoral Associate Baylor College of Medicine Houston, Texas |
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| Dr. Brian Crow | ORSIE Fellow, Centers for Disease Control and Prevention Atlanta, GA |
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| *Dr. Mark Cunningham | Vice President For Institutional Effectiveness Atlanta Metropolitan College, Atlanta, GA |
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| *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 | Associate Professor and Chair Department of Chemistry Georgia Perimeter College Dunwoody, Georgia |
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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 | 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 | ORSIE Fellow, Centers for Disease Control and Prevention Atlanta, GA |
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Representative Publications (of 127)
“The Oxidation of Secondary Alcohols by Dimethyldioxirane: Re-examination of Kinetic Isotope Effects, A.L. Baumstark, P.C. Vasquez, M. Cunningham and P. Leggett-Robinson, submitted to Heterocyclic Communications.
“Epoxidation of α,β-Unsaturated Esters by Dimethyldioxirane,” A.L. Baumstark, P.C. Vasquez, M. Aly and J.P. Sansone, Heterocyclic Communications, in press.
“Synthesis of 4,5-Dihydro-3,4,4,5,5-pentasubstituted-N-Tos-1H-pyrazoles,” P. Truong, G.D. Kennedy, P.C. Vasquez and A.L. Baumstark, Heterocyclic Communications, 2008, 14, 449.
"The Reaction of Alkyl Benzyl Ethers with Dimethyldioxirane: Kinetics," J.W. Jones, P.C. Vasquez and A.L. Baumstark, Heterocyclic Communications, 2008, 14, 11.
“Synthesis of Hexa(methyl/phenyl) Substituted Pyrazoles and Thermolysis to Hexasubstituted Cyclopropanes,” A.L. Baumstark,* G.D. Kennedy, P.C. Vasquez, N. Desalegn and P. Truong, J. Heterocyclic Chem., 2010 47, 1255.
"Synthesis of 4,5-Dihydro-3,4,4,5,5-pentasubstituted-N-Tos-1H-pyrazoles,” P. Truong, G.D. Kennedy, P.C. Vasquez and A.L. Baumstark, Heterocyclic Comm. 2008, in press.
"The Reaction of Alkyl Benzyl Ethers with Dimethyldioxirane,” J.W. Jones, P.C. Vasquez and A.L. Baumstark, Heterocyclic Comm. 2008, 14, 11.
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; Vol I-IV.
- Editorial Board - Heterocyclic Communications, 2003-present.
- Editorial Board - Colonial Academic Alliance Undergraduate Research Journal, 2011-present.