Intramolecular [2+2] photocycloaddition of enone-acetals
✍ Scribed by Michael C. Pirrung; Stephen A. Thomson
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 182 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Lewis acid catalyzed condensation of unsaturated orthofonnates with dienol ethers gives enone-acetals suitable for intramolecular photocycloadditions, yielding heterocyclic precursors to sesquiterpene lactones.
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## Abstract The photochemical reactions of indane‐1‐thiones 4 were examined. Irradiation of indane‐1‐thiones 4c–d bearing δ‐hydrogen atoms in the side chain gave cyclic thiol derivatives 5c–d via δ‐hydrogen atom abstraction by the excited thiocarbonyl sulfur. Irradiation of 2‐allylindane‐1‐thiones
## Abstract The effect of substituents (X H, Me, or F at C(6), R H or Me at C(2′) of the allyl side chain) on the photoisomerization (λ = 350 nm) of 6‐allylcyclohex‐2‐enones 1 in MeCN is studied. Substituents X control the overall efficiency of intramolecular [2 + 2] photocycloadduct formation