David M. Lemal

Professor Lemal received an A.B. degree from Amherst College in 1955 and a Ph.D. from Harvard University in 1959. He became an Instructor at the University of Wisconsin in 1958 and an Assistant Professor in 1960. In 1965 he joined the Dartmouth Chemistry Department as Associate Professor and served as Chairman during 1976-79. In 1981 he was named the Albert W. Smith Professor of Chemistry. He became emeritus in 2006, but continues to conduct research.

Position: Albert W. Smith Professor of Chemistry Emeritus
E-Mail: David M. Lemal 

Research Interests

Professor Lemal's group is interested in the synthesis and chemistry of unusual organic species, both stable and short-lived, and in the mechanism of organic reactions. Their efforts are focused in organofluorine chemistry. Fluorocarbons and derived materials have found a wide variety of applications in commerce and industry, but there is much to be learned about fundamental aspects of the field and a great need for new synthetic methodology. Among the fascinations of this vast area are the dramatic contrasts in properties and chemical behavior which exist between fluorocarbons and their hydrocarbon counterparts. The Lemal research group is engaged in the synthesis and study of target molecules chosen both for the synthetic challenges they pose and for insights they can afford into questions about structure, properties, reactivity and/or mechanism in organofluorine chemistry. Many of the targets incorporate strained rings and/or highly reactive conjugated systems. Orbital topology-controlled reactions figure prominently in this chemistry, and photochemistry plays an important role as a source of both synthetic methods and mechanistic puzzles.

Selected Publications

• Eger, E.I. II; Lemal, D.M.; Laster, M.J.; Liao, M.; Jankowska, K.; Raghavanpillai, A.; Popov, A.V.; Gan, Y.; Lou, Y. "Anesthetic Properties of Some Fluorinated Oxolanes and Oxetanes," Anesthesia and Analgesia 2007, 104, 1090-7.
• Ramanathan, S.; Lemal, D.M. "Conformational and Configurational Dynamics of a Highly Fluorinated Hydrazone," J. Org. Chem. 2007, 72, 1566-9.
• Ramanathan, S.; Lemal, D.M. "Synthesis, Mechanism of Formation, and Dynamics of a Highly Fluorinated Methylenecyclobutene," J. Org. Chem. 2007, 72, 1570-4.
• Chen, X.; Lemal, D.M. “Functionalization of Saturated Fluorocarbons With and Without Light,” J. Fluorine Chem., 2006, 127, 1158-67.
• Chen, X.; Lemal, D.M. “Synthesis and Chemistry of a-Iodoperfluoroacid Esters,” J. Fluorine Chem., 2006, 127, 1137-45.
• Wei, Y.; Liu, Y.; Wong, T.; Lemal, D.M. “Extremely Facile Ring Inversion and Rearrangement in Fluorobicyclo[2.1.0]pentanes,” J. Fluorine Chem. 2006, 127, 688-703.
• Lemal, D.M.; Chen, X. "Fluorinated Cyclobutanes and Their Derivatives" In Cyclobutanes; Liebman, J.F.; Rappoport, Z., Eds.; Wiley: New York, 2005; pp. 955-1029.
• Chen, X.; Lemal, D.M. "Synthesis, Basicity and Dynamics of a Perfluorocyclohexenyl Anion," J. Org. Chem. 2004, 69, 8205-8.
• Wei, Y.; Lemal, D.M. "Novel Concerted Fragmentation upon Alcoholysis of a Urazole," Org. Lett. 2004, 6, 3837-9.
• Lemal, D.M. "Perspective on Fluorocarbon Chemistry," J. Org. Chem. 2004, 69, 1-11.
• He, Y.; Lemal, D.M. "Diels-Alder Reactions of Octafluorobicyclo[2.2.0]hex-1(4)-ene with Aromatics", Org. Lett. 2003, 5, 2135-6.
• Lou, Y.; He, Y.; Kendall, J.T.; Lemal, D.M. “New Syntheses and Chemistry of Hexafluorotropone”, J. Org. Chem. 2003, 68, 3891-5.
• He, Y.; Junk, C.P.; Lemal, D.M. “A Remarkable Propellane”, J. Am. Chem. Soc. 2003, 125, 5590-1.
• Richardson, A.D.; Hedberg, K.; Junk, C.P.; Lemal, D.M., “Electron-Diffraction and Theoretical Investigation of the Structure of Octafluorobicyclo[2.2.0]hex-1(4)-ene in the Gas Phase: Another Example of a Molecule with an Unusually Long C(sp3)-(C(sp3) Single Bond”, J. Phys. Chem. 2003, 107, 3064-8.
• He, Yigang; Lemal, D.M. “A Photoprecursor for Difluorocarbene”, J. Fluorine Chem. 2003, 119, 75-80.
• Lemal, D.M. “Difluoroiodotoluene” In Encyclopedia of Reagents for Organic Synthesis; Wiley, 2003; http://www.mrw.interscience.wiley.com/eros/main.htm.
• Lou, Y.; Chang, J.; Jorgensen, J.; Lemal, D.M. “Octachloroazulene”, J. Am. Chem. Soc. 2002, 124, 15302-15307.
• Lombardi, P.J.; Gan, Y.; Lemal, D.M. “Synthesis and Chemistry of Highly Fluorinated Oxepane-2,7-diols”, Collect. Czech. Chem. Commun. 2002, 67, 1486-1492.