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Al Baumstark

Professor / Organic
Education

B.A. (1970): University of California, Riverside
A.M. (1972) : Harvard University
Ph.D. (1974) : Harvard University
Postdoctoral Fellowship (1974-1976) : Harvard University

Specializations

Organic Chemistry

Biography

Research in my group has centered 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.  These investigationshave provided insights into the limiting factors that control reactivity and selectivity.

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 have 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 have investigated 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.  Selected investigations have centered on epoxidation of electron-poor systems, computational modeling of epoxidation, and heteroatom oxidation.  Recently we have studied epoxidation of cyclic dienes by dimethyldioxirane using DFT calculations to model the epoxidations.

We are in the process of closing the research lab. Current efforts are focused on management of the GSU GA – AL. LSAMP (minority STEM) program and assistance with the GAANN (Ph. D. minority student) program.

 

Honors, Awards, etc.

  1. Junior Faculty Teaching Award, College of Arts and Sciences, GSU, 1982
  2. Camille and Henry Dreyfus Teacher-Scholar Award (1981-86)
  3. Golden Key National Honor Society, GSU Distinguished Research Award (1987-88)
  4. Advances in Oxygenated Processes, Alfons L. Baumstark, Series Editor, JAI Press Inc. Greenwich, Connecticut; 1988 – 1996; Vol I-IV.
  5. Editorial Board – Heterocyclic Communications, 2003-present.
  6. Editorial Board – Colonial Academic Alliance Undergraduate Research Journal, 2011-2014.

 

Honors, Awards, etc.

  1. Junior Faculty Teaching Award, College of Arts and Sciences, GSU, 1982
  2. Camille and Henry Dreyfus Teacher-Scholar Award (1981-86)
  3. Golden Key National Honor Society, GSU Distinguished Research Award (1987-88)
  4. Advances in Oxygenated Processes, Alfons L. Baumstark, Series Editor, JAI Press Inc. Greenwich, Connecticut; 1988 – 1996; Vol I-IV.
  5. Editorial Board – Heterocyclic Communications, 2003-present.
  6. Editorial Board – Colonial Academic Alliance Undergraduate Research Journal, 2011-present.
Publications

Representative Publications (of 132)
“The Synthesis and Chemistry of Structurally Unique Hexasubstituted Pyrazolines,” A.L. Baumstark, P.C. Vasquez and D. McTush-Camp, Heterocyclic Communications, 2013, 19, 13.
“The Monoepoxidation of Acyclic Conjugated Aliphotic Dienes by Dimethyldioxirane,” A.L. Baumstark, P.C. Vasquez, E. Michelena-Baez and H.H. Chen, Heterocyclic Communications, 2012, 18, 75.
“The Reaction of Dimethyldioxirane with 1,3-Cyclohexadiene and 1,3-Cyclooctadiene: Monoepoxidation and Computational Studies,” D. McTush-Camp, P.C. Vasquez and A.L. Baumstark. Heterocyclic Communications., 2015, 21, in press.
“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.

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