Polymeric Separation Media. New Functionalized Polymers for the Selective Removal of Haptens from Complex Organic Mixtures

Abstract

Among the numerous properties of functional polymers, one which has been of interest to us recently is their ability to “fish out”¹ selectively one type of functionality from a complex reaction mixture. Our first contribution² to this field was the development of a polystyryl boronic acid resin which was capable of binding selectively cis-diols. For example, the separation of cis 1,2-cyclohexanediol from its trans isomer could be carried out efficiently by treatment of the commercially available mixture of isomers with the boronic acid resin using either a batch or a column technique². Boronate formation occurs exclusively with the cis diol which is thus retained by the polymer from which it can be cleaved later by addition of moist solvent or alcohol. This method can also be used with 1,3 or 1,4 diols and is of particular value with carbohydrate derivatives^3–4 Other noteworthy applications of functional polymers, in which their ability to extract a component from a complex mixture is used for synthetic purposes, include the preparation of a threaded macrocycle⁵, the synthesis of an unsymmetrical tetraarylporphyrin⁶, and the preparation of a dideoxy-sugar of biological importance such as methyl α-D-paratoside¹.