Investigation of the reaction conditions that control benzylic bromination vs electrophilic aromatic substitution in electron rich aromatic systems

CHED 419

Andre Boustani, Andre-Boustani@utulsa.edu, Department of Chemistry and Biochemistry, University of Tulsa, 600 South College Ave, Tulsa, OK 74104, John Richardson, School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, 311 Ferst Drive, N.W, Atlanta, GA 30332, Christopher W. Jones, christopher.jones@chbe.gatech.edu, School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, 311 Ferst Drive, NW, Atlanta, GA 30332-0400, and John C. DiCesare, john-dicesare@utulsa.edu, Department of Chemistry and Biochemistry, The University of Tulsa, 600 South College Ave, Tulsa, OK 74104.
In an ongoing study on the synthesis of functionalized phosphine pincer compounds for the coordination of various metals for use as catalysts we have need for a selective benzylic bromination reaction. Traditional reaction conditions using NBS and AIBN at elevated temperatures leads to a significant amount of aromatic ring bromination. This paper will discuss our attempts to develop a low temperature benzylic bromination reaction with minimal electrophilic aromatic substitution byproducts.
 

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

Division of Chemical Education

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