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.

• This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

Creator

• Tsefrikas, Vikki Marie

Publisher

• Worcester Polytechnic Institute

Identifier

• 01D151M

Advisor

• Pavlik, James W.

Year

• 2001

Date created

• 2001-01-01

Resource type

• Major Qualifying Project

Major

• Chemistry

Rights statement

• In Copyright