Faculty Advisor

Pavlik, James W.

Abstract

2-phenylthiazole was synthesized from bromoacetaldehyde diethyl acetal and thiobenzamide. The photochemistry of 2-phenylthiazole was studied upon irradiation at 254nm and with light of wavelenghth >290nm in methanol, acetonitrile, and hexane solvents. In addition to the previously observed phototransposition to yield 3-phenylisothiazole, 4-phenylthiazole, and 5-phenylisothiazole, 2-phenylthiazole was observed to undergo photofragmentation to yield benzonitrile. The yield of benzonitrile was highest (2%) upon irradiation in methanol at 254nm and lowest upon irradiation in acetonitrile at >290nm. The yields of the phototransposition products was also found to depend on the wavelength of light used for irradiation. When >290nm light was used, the amount of 4-phenylthiazole produced increased, while the amounts of the other phototransposition products decreased. 5-Deuterio-2-phenylthiazole was also synthesized and its photochemistry studied to further examine the phototransposition mechanism of 2-phenylthiazole. 5-Deuterio-2-phenylthiazole was irradiated in acetonitrile and with light 254nm to maximize the yield of the 3-phenylisothiazole phototransposition product. This product was isolated, and the location of the deuterium examined.

Publisher

Worcester Polytechnic Institute

Date Accepted

January 2000

Major

Chemistry

Project Type

Major Qualifying Project

Accessibility

Restricted-WPI community only

Advisor Department

Chemistry and Biochemistry

Share

COinS