Ronald Magid Professor Organic Chemistry Substitution reactions of allylic compounds B.S., Yale University (1959) M.S., Yale University (1960) Ph.D., Yale University (1964)
E-mail: magid@ion.chem.utk.edu Representative publications   ·   Biographical sketch

Research

Allylic compounds (CH₂=CH-CH₂-X and derivatives) have been of synthetic, mechanistic, and biochemical importance for more than fifty years. Among the most fascinating aspects of their behavior, the stereochemistry and regiochemistry of their substitution reactions with nucleophiles and organometallic reagents have received considerable attention.

When CH₂=CH-CH₂-X reacts with a nucleophile Y, attack can occur either at the alpha-carbon (SN₂ reaction) or at the gamma-carbon with rearrangement of the double bond (SN₂' reaction). The exact product distribution depends on the substrate, the nucleophile, the leaving group, and the solvent. Organometallic compounds, similarly, can attack either or both of the carbon centers. My students and I are engaged in a broad series of studies designed to elucidate not only the factors which determine the site of attack but also the stereochemistry of reaction at each center. These projects entail the syntheses of optically active, deuterium-labeled allylic compounds and the analyses of product mixtures using chromatography, nmr spectroscopy, and polarimetry.

Representative publications

Nucleophilic and organometallic displacement reactions of allylic compounds: stereo- and regiochemistry. R.M. Magid, Tetrahedron 36, 1901 (1980).

Improvements in the hexachloroacetone/triphenylphosphine procedure for the conversion of allylic alcohols into chlorides. R.M. Magid, B.G. Talley, and S.K. Souther, J. Org. Chem. 46, 824 (1981).

"Triphenylphosphine-Hexachloroacetone", in Vol. 8 of Encyclopedia of Reagents for Organic Synthesis, L.A. Paquette, Ed. (Wiley: Chichester, 1995).

Biographical sketch

Dr. Magid received the B.S. degree in chemistry from Yale University in 1959. He attended graduate school at Yale University, receiving the M.S. degree in 1960 and the Ph.D. in 1964. He performed postdoctoral research at Stanford University as a National Research Council before joining the faculty of the University of Tennessee in 1970. He is a member of Phi Beta Kappa and has received several teaching awards at the University of Tennessee.