Bis(oxazoline) copper(II) catalysis of the Diels-Alder reaction

CHED 357

Edward G. Franklin, frankli357@duq.edu, Jason DeChancie, jdechancie@hotmail.com, and Jeffrey D. Evanseck, evanseck@duq.edu. Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Ave., 308 Mellon Hall, Pittsburgh, PA 15282
Computer modeling of the catalytic effect of bis(oxazoline) copper(II) complexes on the rate and selectivity of Diels-Alder reactions has been performed. The steric and electronic effects of tert-butyl, isopropyl, and phenyl substitution are reported with regard to the reaction of cyclopentadiene and acrylate imide. The computer modeling provides a detailed physical understanding of how C2-substituent variation of the catalyst controls the rate and selectivity of the Diels-Alder reaction. The computations are in excellent agreement with available experimental data and a new fundamental understanding of bis(oxazoline) copper(II) catalytic action will be discussed.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix: LSAMP/REU Poster Session
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Chemical Education

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006