Abstract:
An unprecedented reaction, the base-catalyzed fragmentation of pentafluorobenzylic alcohols, was investigated. Studies on a variety of C6F5-derived alcohols show that a dual reaction pathway occurs in mixed solvent systems such as DMSO and methanol. 19F NMR and GC-MS analyses have been used to examine the mechanism of the fragmenation. Other reaction variables, which involved changing the base and/or solvent conditions, have been studied to determine their effect on fragmentation. The relative rates of reactivity of a variety of pentafluorobenzylic alcohols were determined.
A new technique to screen metal catalysts rapidly via GC-MS using modified injection port liners has been developed. A variety of interesting reactions of organic molecules catalyzed by metal salts in the gas phase have been discovered. This technique has also been applied to the fragmentation reactions above.
