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. 2003 Apr 4;68(7):2839-43.
doi: 10.1021/jo020599g.

Ene Hydroperoxidation of Isobutenylarenes Within Dye-Exchanged Zeolite Na-Y: Control of Site Selectivity by Cation-Arene Interactions

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Ene Hydroperoxidation of Isobutenylarenes Within Dye-Exchanged Zeolite Na-Y: Control of Site Selectivity by Cation-Arene Interactions

Manolis Stratakis et al. J Org Chem. .

Abstract

The site selectivity in the singlet oxygen ene reaction of several deuterium-labeled isobutenylarenes depends on the position and the electronic nature of the aryl substitutents. For example, 1-(4-trifluoromethylphenyl)-2-methylpropene gives 82% twin selectivity whereas the isomeric 1-(2-trifluoromethylphenyl)-2-methylpropene gives 68% twix selectivity. If photooxygenation of these CF(3)-substituted compounds is carried out in solution, the opposite selectivity trends are found. On the basis of DFT calculations, these results are rationalized in terms of oxygen-cation and cation-arene interactions.

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