Trapping of 1,4-diradical intermediate in intramolecular [2+2] photocycloaddition
β Scribed by D. Becker; N. Haddad; Y. Sahali
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 234 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
For the first time a 1,4-diradical intermediate u was trapped in 43% yield in an intramolecular [2+2] photocycloaddition of olefins to cyclohexenone. The results support the assumption that the first bond is formed to carbon-p of the enone system.
π SIMILAR VOLUMES
Complete trapping of 1.4~diradical intermediates, formed in the intramolecular [2+2] photocycloaddition of 13. provide direct evidence for the exclusive formation of the first bond at the C(8) of the cyclic enone. This result is found in full agreement with the previously studied compounds 1. Copyr
## Abstract The photochemical reactions of indaneβ1βthiones 4 were examined. Irradiation of indaneβ1βthiones 4cβd bearing Ξ΄βhydrogen atoms in the side chain gave cyclic thiol derivatives 5cβd via Ξ΄βhydrogen atom abstraction by the excited thiocarbonyl sulfur. Irradiation of 2βallylindaneβ1βthiones
Intramolecular [3+2] -photocyctoadditions of alkenyl methyl 1,4-naphthalenedicarboxylates, which contain rather remote alkene moieties corresponding to isobutene or a-methylstyrene, proceeded largely depending on the chain lengths to give [3+2]-adducts having nine-to eleven-membered ring systems as