Catalyzing Methanolysis of Alkyl Halides in the Interior of an Amphiphilic Molecular Basket
A molecular basket with four cholate units assembled on a cone-shaped calixarene assumed reversed micelle-like conformation in 5% methanol/carbon tetrachloride. The inwardly facing hydroxyl groups on the cholates concentrated the polar solvent from the mostly nonpolar mixture. Methanolysis of alkyl halides benefited from the concentrated pocket of methanol if the substrate was capable of entering the basket. Substrates that were too large or too hydrophobic to fit within the basket showed no rate acceleration.
Reprinted (adapted) with permission from Organic Letters 9 (2007): 5147, doi:10.1021/ol701883u. Copyright 2007 American Chemical Society.