Pavlik, James W.
4-methyl-5-phenyl (F=0.43+/-0.02) and 5-methyl-4-phenyl- isoxazoles (F=0.45+/-0.01) were observed to undergo phototransposition to 4-methyl-5-phenyl and 5-methyl-4- phenyloxazoles and photocleavage to yield a-benzoyl- propionitrile and a-phenylacetoacetontrile respectively upon irradiation in methanol. Photochemical excitation of 4-methyl-5-phenylisoxazole is suggested to result in cleavage of the O-N hetrobond leading to the formation of a vinyl nitrene, which was also generated by photolysis and thermolysis of 2-benzoyl-2methyl-2H-azirine, a suspected intermediate in the photoreaction of 4-methyl-5-phenylisoxazole.
Worcester Polytechnic Institute
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Chemistry and Biochemistry