Ian Rosenstein
Chair, Associate Professor of Chemistry
Ian Rosenstein's research focuses on the development on new methods for the synthesis of organic compounds using free radicals as key reactive intermediates. Much of Rosenstein's work has explored the use of chiral auxiliaries for controlling the stereochemistry of radical addition reactions. His current work is aimed at developing methodology that combines radical processes with metal-catalyzed coupling reactions to construct multiple carbon-carbon bonds in a single reaction sequence. Rosenstein joined the Hamilton faculty in 1994 after completing his doctorate and a year of postdoctoral study at Duke University.
Recent Courses Taught
Advanced Organic Chemistry I
Advanced Organic Chemistry II
Organic Chemistry I
Organic Chemistry II
Chemistry Research
Research Methods in Chemistry
Distinctions
- Samuel and Helen Lang Prize for Excellence in Teaching, Hamilton College, 2012
- NSF-MRI Grant, “Acquisition of a High Field NMR for Chemistry Research,” March 1, 2004-Feb. 28, 2007, co-PI (Robin Kinnel, PI)
- NSF CCLI Grant, “Calorimetry and Capillary Electrophoresis in the Undergraduate Teaching Laboratory,” July 1999-June 30, 2001, co-PI (Timothy Elgren, PI)
- John R. Hatch Class of 1925 Excellence in Teaching Award, Hamilton College, 1999
- American Chemical Society-Petroleum Research Fund Type G Grant, "Is a Dipolar Transition State Involved in the Free Radical Induced Ring Opening of Strained Ring Systems?," July 1996-June 1998
- Pew-New York State Cluster Faculty/Student Summer Research Program, summer 1995
- Howard Hughes Medical Institute Summer Research Stipend, 1995
Selected Publications
- Kinnel, R. B.; Van Wynsberghe, A. W.; Rosenstein, I. J.; Brewer, K. S.; Cotten, M.; Shields, G. C.; Borton, C. J.; Senior, S. Z.; Rahn, G. R.; Elgren, T. E. “A Departmental Focus on High Impact Undergraduate Research Experiences,” in Developing and Maintaining a Successful Undergraduate Research Program; Chapp, T. W.; Benvenuto, M. A., Eds.; ACS Symposium Series 1156; American Chemical Society: Washington, D. C., 2013, pp. 5-22.
- Otley, K. D.*; Saccomano, B. W.*; McKee, S. A.*; Nizialek, G. A.*; Hamilton, D. S.*; Sherrow, L. K.*; Jones, C. Y.; Rosenstein, I. J. "Synthesis of Three Selectively Deuterated Propylene Oxides," J. Labelled Compd. Radiopharm., 2011, 54, 308.
- Rosenstein, I. J. “Bis((1R,2S,5R)-menthyl)(phenyl)tin hydride,” Electronic Encyclopedia of Reagents in Organic Synthesis, 2005.
- Rosenstein, I. J. “A Literature Exercise Using SciFinder Scholar for the Sophomore Organic Course,” J. Chem. Ed., 2005, 82, 652.
- Rosenstein, I. J. “Radical Fragmentation Reactions,” in Radicals in Organic Synthesis, Vol. 1; Renaud, P., Sibi, M.P., Eds.; Wiley-VCH: Weinheim, 2001.
- Rosenstein, I. J.; Tynan, T.A.* “Imine Derivatives of Fumaraldehyde From Oxidation of a β-Aziridinyl Alcohol,” Synthetic Comm., 2000, 30, 1447.
- Rosenstein, I. J.; Tynan, T.A.* "Chiral Auxiliary Mediated Stereoselective Allylation of Electron Deficient Radicals," Tetrahedron Lett. 1998, 39, 8429.
- Porter, N. A.; Rosenstein, I. J. “Stereoselective Radical-Radical Disproportionation,” Tetrahedron Lett., 1993, 34, 7865.
- Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. “The Stereoselective Synthesis of Succinamide Derivatives via Enolate Oxidative Coupling,” Tetrahedron Lett., 1993, 34, 4457.
- Porter, N. A.; Rosenstein, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W.- X.; McPhail, A. T. "Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups," J. Am. Chem. Soc., 1992, 114, 7664.
- Porter, N. A.; Bruhnke, J. D.; Wu, W.- X.; Rosenstein, I. J.; Breyer, R. "Control of Stereochemistry in Free Radical Reactions with Oxazolidine Auxiliaries," J. Am. Chem. Soc. 1991, 113, 7788.
- Porter, N. A.; Scott, D. M. ; Rosenstein, I. J.; Giese, B.; Veit, A.; Zeitz, H. G. "Stereoselective Intermolecular Radical Additions to Amide-Substituted Alkenes," J. Am. Chem. Soc. 1991, 113, 1791.
Professional Affiliations
American Chemical Society, 1989-present
Phi Lambda Upsilon, 1989-present
Sigma Xi, Hamilton College Chapter, 1995-present; vice president 1997-98; president 1999-2000
Project Kaleidoscope, Faculty for the 21st Century, 2000-present
Appointed to the Faculty
1994Educational Background
Ph.D., Duke University
B.S., Massachusetts Institute of Technology
