| Abstract: | Various α-halo-p-xylenes have been polymerized with base yielding p-xylylene polymers. The reaction involves a 1,6-dehydrohalogenation to give a xylylene which then polymerizes. α,α′-Dichloro-p-xylene forms poly-α-chloro-p-xylylene and polymers containing stilbene units; α,α,α′,α′-tetrachloro-p-xylene gives poly-α,α,α′-trichloro-p-xylylene; alkyl, aryl, and halogen ring-substituted α-chloro-p-xylenes give the corresponding ring-substituted poly-p-xylylenes. The more halogens in the α positions (up to five), the weaker the base necessary for dehydrohalogenation. Sodium hydroxide in methanol will polymerize tetrachloro-p-xylene, while potassium tert-butoxide in refluxing p-xylene is necessary to polymerize α-chloro-p-xylenes. Stilbenes are formed when α-halo-p-xylenes are reacted with potassium tert-butoxide in polar solvents such as dimethyl sulfoxide. |
