Pavlik, James W.
The synthesis and photochemistry of 3-phenyl-5- (trifluoromethyl) isoxazole was studied. It was found that, upon irradiation at 254nm in methanol solvent, 3-phenyl-5-(trifluoromethyl) isoxazole photoreacts to form 5-methoxy-3-phenyl-5- (trifluoromethyl)-4, 5-dihydroisoxazole in 7% yield. A second photoproduct was obtained from this reaction in 28.6% yield, suggested to be a diastereomeric mixture of two compounds whose exact structures were not elucidated. Evidence that this photoproduct exists as diastereomers is given by GC and GC/MS analysis.
Worcester Polytechnic Institute
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Chemistry and Biochemistry