Abstract
Functionalization reactions of poly(styryl)lithium with N-(benzylidene)-trimethylsilylamine produce polymers containing significant amounts of coupling products for Mn = 2.8 × 103g/mol (19% coupling) and Mn = 15 × 103g/mol (15% coupling). Isolation and characterization of the products for the amination of poly(styryl)lithium with Mn = 2.8 × 13g/mol indicates that the non-coupled products consist of a primary amine-terminated polymer (69% yield) and an acetophenone-type functionalized polymer (12% yield). The dimeric product (19% yield) has a primary amine functional group. The formation of these products is rationalized by a Cannizzaro-type reaction of the initially formed polymeric lithium silylamide product with excess N-(benzylidene)(trimethylsilylamine to form the corresponding polymer with imine chain-end functionality which can react with another molecule of poly(styryl)lithium to form dimer product or hydrolyze to the acetophenone functionality on work-up.
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