FLUOROAROMATIC CHEMISTRY: THE REACTIONS AND KINETICS OF SODIUM PENTAFLUOROPHENOLATE WITH SUBSTITUTED PENTAFLUOROBENZENES
Abstract
Sodium pentafluorophenolate and sodium 4-hydrotetrafluorophenolate were synthesized and shown to react with a series of substituted pentafluorobenzenes. Reaction conditions were chosen to maximize the kinetically controlled product, viz phenolate substitution at the position para to the functional group. Small percentages of side products derived from ortho or both ortho and para displacement were generally observed. Polysubstitution products could be obtained in fair yield when pentafluorobenzonitrile was used as the substrate. The relative rates for the reaction of eight substituted pentafluorobenzenes with sodium pentafluorophenolate were measured. The differences in rate between substituents were relatively large. This was further demonstrated by the linear plot of log (relative rate) vs Hammet's sigma P which gave a slope of about 7.5.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1967
- Accession Number
- AD0815443
Entities
People
- Christ Tamborski
- Ralph J. Depasquale
Organizations
- Air Force Research Laboratory