Separable, soluble polystyrene supports in synthesis and catalysis

ORGN 593

Patrick N. Hamilton, phamilton@mail.chem.tamu.edu, David E. Bergbreiter, bergbreiter@tamu.edu, and Andrew M. Shuff, andrewshuff@tamu.edu. Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842
Alternative poly(4-alkylstyrene)s soluble polymer supports for synthesis and catalysis will be discussed. Such supports can be separated from products using their phase selective solubility in heptane. Soluble copolymers of chloromethylstyrene and 4-alkylstyrenes that are analogs of known insoluble Merrifield and soluble styrene copolymers used in synthesis were prepared. Reagents, catalysts or dyes were then bound to the resulting chloromethylstyrene-4-alkylstyrene copolymer and were separated in simple liquid/liquid separations. In a typical experiment, a dye labeled copolymer was prepared and dissolved in a miscible mixture of heptane and ethanol-water or heptane and dimethylacetamide. Then the miscible solvent mixture was perturbed into a biphasic state by cooling or by addition of a small amount of a perturbant. Varying the size of the alkyl groups affected the phase selective solubility of the poly(4-alkylstyrene) and increased the separability of copolymer supported species in synthesis.