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
Copyright Statement
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Accessibility
Restricted-WPI community only
Advisor Department
Chemistry and Biochemistry
Advisor Program
Chemistry and Biochemistry