Collect. Czech. Chem. Commun. 1987, 52, 2204-2211

Polymer sulfoxides based on poly(vinyl alcohol) as effective catalysts of nucleophilic substitution reactions

Hana Hrudková, Pavel Čefelín and Václav Janout

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


Using the addition of alcohols to ethyl vinyl sulfoxide, a number of 2-alkoxyethyl ethyl sulfoxides were prepared, containing the following alkyls: methyl, ethyl, isopropyl, benzyl, and cyclohexyl. With a 10 mole % excess of alcohol the extent of the reaction was 70-95%. By a polymeranalogous reaction with poly(vinyl alcohol) and poly(ethylene-co-vinyl alcohol), copolymers poly[1-hydroxyethylene (74 mole %)-co-1-(2-ethylsulfinylethoxy)ethylene (26 mole %)] and poly[ethylene (62 mole %)-co-1-hydroxyethylene (35 mole %)-co-1-(2-ethylsulfinylethoxy)ethylene (3 mole %)] were prepared; the reaction with polymer alcohols requires the use of excess ethyl vinyl sulfoxide. These polymer sulfoxides were tested as catalysts of nucleophilic substitution reactions, using reactions of 1-bromooctane with sodium phenoxide, sodium iodide and potassium thiocyanate. They are more effective catalysts than polymer sulfoxides based on crosslinked poly(styrene) under the conditions of a two-phase (S-L) and three-phase (L-S-L) catalysis.