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

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.