Investigation of the difluoromethyl group as an activator for nucleophilic aromatic substitution

POLY 357

Robert W. Kopitzke, rkopitzke@winona.edu, Winona State University, Winona, MN 55987 and Ray Gunawidjaja, rayguna@iastate.edu, Materials Science and Engineering, Iowa State University, Ames, IA 50011.
The difluoromethyl group was investigated as an activator for nucleophilic aromatic substitution. The difluoromethyl bearing monomer, bis-(4-fluorophenyl)- difluoromethane was synthesized in two steps from 4,4′-difluorobenzophenone. Model studies were done with two equivalents of phenol under varying reaction conditions and evaluated using GC/MS. The most successful reaction resulted in 96.1% conversion to the disubstitution product after 24 hours at 195 °C in NMP. In contrast, the benzophenone derivative reacted almost quantitatively in 4 hours in NMP at 175 °C.
 

General Papers
6:00 PM-8:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Division of Polymer Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005