LITHIATION, MERCURIATION, AND THALLIATION OF POLY(N-VINYLCARBAZOLE) - CHEMICAL-TRANSFORMATIONS OF THE PRODUCTS

N-vinylcarbazole was homopolymerized or was copolymerized with divinylbenzene (2% and 4%) using AIBN as initiator. The linear homopolymer was shown not to undergo direct lithiation using n-butyllithium, but lithiation was achieved using n-butyllithium and brominated linear poly(N-vinylcarbazole). The polymers reacted smoothly with mercury(II) acetate or trifluoroacetate in THF or dichloromethane to give mercuriated polymers with high degrees of substitution (approx. 80%); with thallium(III) trifluoroacetate in dichloromethane a thalliated polymer was formed, but with a lower degree of substitution (approx. 20%). The mercuriated and thalliated polymers reacted with iodine (or potassium iodide) to give polymers containing an iodo-substituent.