Aromatic Nucleophilic Substitution Polymerization of Dichloro-1,3,5-Triazines with Alkanedithiols

Reaction of 2,4-dichloro-6-phenyl-1,3,5-triazine with alkane-dithiols in the presence of a base in THF afforded the corresponding condensation polymers containing triazinylthio group in moderate yields. This polymerization reaction also proceeded in the o-dichlorobenzene-water two-phase system by using phase transfer catalysts. The resulting polymers consisted of THF-soluble and insoluble fractions. When the reaction was carried out at a higher temperature or for a longer reaction time, the yield of the insoluble polymer was increased. The THF-soluble polymers were also soluble in toluene, and they had the ability to extract sodium and potassium ions from aqueous picrates. The polymers functioned as catalysts for substitution reactions of an alkyl bromide and the reduction of a ketone with sodium borohydride under liquid-liquid phase transfer conditions with a reactivity superior to that of the monomeric analog.