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Exploiting Aggregation To Achieve Phase Separation in Macrocyclization

Authors

  • Anne-Catherine Bédard,

    1. Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7 (Canada), Fax: (+1) (514)-343-7586
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  • Prof. Dr. Shawn K. Collins

    Corresponding author
    1. Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7 (Canada), Fax: (+1) (514)-343-7586
    • Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7 (Canada), Fax: (+1) (514)-343-7586
    Search for more papers by this author

Abstract

The aggregation properties of poly(ethylene glycol) (PEG) can be exploited in organic synthesis to control dilution effects. Through the use of solvent mixtures containing PEG400/MeOH, macrocyclization by Glaser–Hay coupling can be conducted at high concentrations. The origin of the selectivity has been studied by using surface tension measurements, UV spectroscopy, and chemical tagging and demonstrates the dependence of the yield and selectivity on the aggregation of PEG400 and its ability to preferentially solubilize organic substrates, resulting in a phase separation from the catalyst system.

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