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2005
Oxazole derivatives
R 0220
Photochemistry of 4- and 5-Phenyl Substituted Isoxazoles. — Substituted isoxa(I), (IV), (VI), and (IX) undergo phototransposition via a pathway involving only
32- 132 zoles
interchange of the N-2 and C-3 ring position. Additionally, the phototransposition of
isoxazoles (I), (VI), and (IX) is accompanied by a photo-ring cleavage. The effect of a
trifluoromethyl substituent on the photochemistry of 5-phenylisoxazole (I) is demonstrated with compound (XII). Irradiation of (XII) in methanol leads to a substantial decrease in the yield of phototransposition product (XIV) and to the formation of a mixture of the diastereomeric aziridines (XV) and (XVI). However, upon irradiation in acetonitrile, the only product obtained is (XIV). — (PAVLIK*, J. W.; MARTIN, H. S.;
LAMBERT, K. A.; LOWELL, J. A.; TSEFRIKAS, V. M.; EDDINS, C. K.; KEBEDE,
N.; J. Heterocycl. Chem. 42 (2005) 2, 273-281; Dep. Chem. Biochem., Worcester
Polytech. Inst., Worcester, MA 01609, USA; Eng.) — H. Hoennerscheid
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