The synthesis of diene and of vinyl copolymers containing predetermined quantities of polynuclear hydrocarbon or heterocyclic adducts-III. Copolymers formed from polynuclear hydrocarbons and alkyldihalides

Abstract

The reaction in tetrahydrofuran between the disodium salt of anthracene (A) and alkyl dihalides (RX 2) results in oligomeric products with a repeat unit -[A-R]-. The same reaction with the dilithium derivative is complicated by the high reactivity of this species toward solvent; oligomers with -(CH 2) 4OH end groups are isolated. The xylylene dihalides undergo metallation and Wurtz coupling, and they produce low yields of oligomers rich in xylylene units. The reaction with dilithium acenaphthylene and alkyl dihalides gives a high yield of copolymer but there is evidence of crosslinking. Although addition occurs principally across the 1.2 position, some 1,5 addition is believed to cause this crosslinking. With dilithium phenanthrene the reaction is mainly one of electron transfer; the oligomers produced in low yield are low in phenanthrene adducts.