Journal of Organic Chemistry p. 4011 - 4019 (1990)
Update date:2022-08-05
Sauers, R. R.
Hadel, L. M.
Scimone, A. A.
Stevenson, T. A.
The photochemistry of 4-acylisoxazoles 4, 5, 13, 14, and 17 was investigated in an effort to clarify literature contradictions and anomalies and to provide a more detailed picture of the nature and number of intermediates involved in photoreactions of these systems.In contrast to a previous report on the photorearrangement of 14, both oxazoles expected from a 2H-azirine intermediate have been observed.Wavelength studies of 5 and the derived 2H-azirine 10 revealed evidence for the involvement of at least two distinct product-forming intermediates.The results of quantum yield and laser photolysis measurements for ketones 4, 14, and 17 have been interpreted in terms of rapid openings of triplet states to form diradical-like intermediates coupled with efficient reclosures (70-99percent).
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