Direct irradiation of 5,5-diaryl-2,5\_dihydrofurans results in a di-r-methane rearrangement to give 3-penten-l-one derivatives. Triplet sensitization leads to the formation of a 2-oxabicyclo[2.l.O]pentane which is extremely sensitive to heat and oxygen. The light-induced transformations of the five
The photochemical rearrangement of 2,5-diphenyloxazole
โ Scribed by Masaharu Kojima; Minoru Maeda
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 133 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Recently, it has been reported that the five-membered heterocyclic compounds containing two vicinal hetero-atoms interchanged their positions to 1,3-systems as a common mode of reaction when irradiated with ultraviolet light.
Examples include the photo-induced rearrangement of indazoles to benzimidazoles(Z), pyrazole to imidazole(2), 3,5-diphenylisoxazole to 2,5-diphenyloxazole(3), benzisoxazoles to benzoxazoles(4), and 1,3,5-trimethylpyrazole to 1,2,4-trimethylimidazole(5).
On the other hand, there is no record of the rearrangement of 1,3-to 1,2system.
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The dramatic photochemical rearrangements of santonin and other 2,5-cyclohexadienones 3 contrast sharply with the reported photodimerizations of 2-cyclohexenones. It has been generally assumed that the complex photochemical rearrangements of the 2,5-cyclohexadienones are not possible with simple E-c