H-abstraction prevails over α-cleavage in the solution and solid state photochemistry of cis-2,6-di(1-cyclohexenyl)cyclohexanone
✍ Scribed by Christopher J. Mortko; Hung Dang; Luis M. Campos; Miguel A. Garcı́a-Garibay
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 163 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The photochemistry of cis-2,6-di(1-cyclohexenyl)cyclohexanone was studied in solution and in crystals to determine its photoreactivity and chemoselectivity. Although 1,3-acyl shifts and the oxadi-p-methane rearrangement products are possible for the b,g-unsaturated chromophore, an efficient intramolecular abstraction of an allylic g-hydrogen and small amounts of a-cleavage and decarbonylation were observed. The mechanism of the Norrish type-II reaction and the selectivity of product formation were analyzed in terms of structural information obtained by X-ray diffraction analysis.