Collect. Czech. Chem. Commun. 1989, 54, 1830-1838

Solid phase cosolvents: Polymer analogs of N,N-dialkylamides based on polystyrene

Václav Janout, Hana Hrudková, Bohumír Valter and Pavel Čefelín

Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, 162 06 Prague 6


Polymers of styrene of various type can be readily amidomethylated by a reaction with N-(hydroxymethyl)amides. Analogs of N-methyl-2-pyrrolidone, N-methyl-6-hexanelactam, N-methyl-8-octanelactam, and N,N-dimethylacetamide were prepared by the polymeranalogous amidomethylation. The reaction between poly(styrene-co-divinylbenzene) and N-(hydroxymethyl)-2-pyrrolidone proceeds by an acceleration mechanism. The extent of the reaction depends on the structure of the polymer and N-(hydroxymethylamide), on the concentration of the catalyst (trifluoroacetic acid) and on the way in which the polymer swells before the reaction. Polymers with bound residues of N-methylamide as solid cosolvents are catalysts of the model nucleophilic substitution reaction between sodium phenoxide and 1-bromooctane. A distinct polymer effect was recorded with polymer analogs of N-methyl-2-pyrrolidone in this reaction.