Faculty Advisor

Pavlik, James W.

Abstract

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.

Publisher

Worcester Polytechnic Institute

Date Accepted

January 2001

Major

Chemistry

Project Type

Major Qualifying Project

Accessibility

Restricted-WPI community only

Advisor Department

Chemistry and Biochemistry

Advisor Program

Chemistry and Biochemistry

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