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Pure Appl. Chem. Vol. 72, No. 12, pp. 2289-2298 (2000)

Pure and Applied Chemistry

Vol. 72, Issue 12

Microreactor-controlled selectivity in organic photochemical reactions*

Chen-Ho Tung**, Li-Zhu Wu, Li-Ping Zhang, Hong-Ru Li, Xiu-Yu Yi, Kai Song, Ming Xu, Zhen-Yu Yuan, Jing-Qu Guan, Hong-Wei Wang, Yun-Ming Ying, and Xiao-He Xu

Institute of Photographic Chemistry, Chinese Academy of Sciences, Beijing 100101, China

Abstract: Molecular-sieve zeolites, Nafion membranes, low-density polyethylene films, and mixed surfactant vesicles have been used as microreactors to carry out organic photochemical reactions. The photo-cycloadditions of diaryl compounds with long flexible chains included in NaY zeolite or low-density polyethylene films yield intramolecular photocyclomers to the exclusion of intermolecular products. The photosensitized oxidation of alkenes included in pentasil zeolites or Nafion membranes or vesicles can be directed selectively toward either the singlet oxygen-mediated or the superoxide radical anion-mediated products by controlling the status and location of the substrate and sensitizer molecules in the reaction media. The photo-Fries rearrangement of phenyl phenylacetates included within NaY and pentasil zeolites or Nafion membranes gives either ortho-hydroxyphenones or decarbonylation products depending on the size/shape of the microreactors and the substrate molecules. All these results demonstrate the utility of microreactors to control the product selectivity in organic photochemical reactions.

*Plenary lecture presented at the 15th International Conference on Physical Organic Chemistry (ICPOC 15), Göteborg, Sweden, 8 –13 July 2000. Other presentations are published in this issue, pp. 2219 –2358.
**Corresponding author

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