Pavlik, James W.
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.
Worcester Polytechnic Institute
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Chemistry and Biochemistry