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- Title
Photoaddition Reactions of Benzoxazole-2(3H)-thiones to Cycloalkenes and Heteroaromatics.
- Authors
Takehiko Nishio; Kiyoko Shiwa; Masami Sakamoto
- Abstract
Photoaddition reactions of benzoxazole-2-thiones 1 with cycloalkenes 2 and heteroaromatics 3 were examined. Irradiation of N-acylbenzoxazole-2-thiones 1a and 1b, and 3-(methoxycarbonyl)- and 3-(phenoxycarbonyl)benzoxazole-2(3H)-thiones (1f and 1h, resp.) in the presence of cycloalkenes 2a2c, cyclohexa-1,4-diene (2d), and indene (2e) yielded 2-substituted benzoxazoles 413, 18 and 19, and iminothietanes 1417, by intramolecular trapping of the acyl or MeOCO and PhOCO groups by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic amino-thietanes AT formed by [2+2] cycloaddition of the C=S bond of 1 and C=C bond of 2. Irradiation of 1 in the presence of heteroaromatics 3 gave the 2-substituted benzoxazoles 2033 exclusively.
- Subjects
AROMATIC compounds; IRRADIATION; CYCLOALKANES; PYRROLES
- Publication
Helvetica Chimica Acta, 2003, Vol 86, Issue 10, p3255
- ISSN
0018-019X
- Publication type
Article