Reaction of polyion-radicals derived from polymers containing naphthalene residues with aryl and alkyl halides

The reactions of alkali metal adducts of polymers containing naphthalene groups with alkyl and aryl halides were compared with those of alkali metal naphthalene adducts. Poly-I-vinyl naphthalene, ter-poly-1-vinyl naphthalene-styrene-divinyl benzene and polyacenaphthylene were used. It was found that the alkali metal adducts of naphthalene alone and of polyacenaphthylene reacted similarly while those of naphthalene substituted on a vinyl polymer backbone reacted selectively. No reaction took place with halogen substituted on an aromatic or alicyclic ring, such as haloderivatives of benzene, naphthalene and cyclohexane. Aliphatic and benzylic organic halides reacted similarly with alkali metal naphthalene or with alkali metal adduct of poly-l-vinyl naphthalene. The results were attributed to the conformation of the alkali metal adduct of poly-l-vinyl naphthalene.