The living C1 polymerization of ylides allows for the production of linear hydrocarbon polymers with controlled molecular weight, polydispersity and well-defined topology. Sulfoxide ylides are the most common C1 monomers. For example, dimethylsulfoxonium methylide is used to produce low molecular weight linear, highly crystalline polymethylene with a narrow molecular weight distribution. Secondary ylides such as (dimethylamino)phenyloxosulfonium ethylide have been employed to synthesize substituted carbon backbones. In this work we report a new, convenient source of the ethylidene monomer for the introduction of branched groups in the carbon backbone. The monomer precursor, triethylsulfoxonium chloride (Et3SOCl), was synthesized in 74% overall yield in 3 steps. Copolymers of dimethylsulfoxonium methylide and diethylsulfoxonium ethylide yield materials with the same composition as an ethylene-propylene copolymer. The copolymers were synthesized with control of molecular weight, monomer composition and narrow polydispersity. 

Synthesis of poly(methylidene-<i>co</i>-ethylidene) with a new secondary ylide monomer via C1 polymerization

248th National Meeting (2014)

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Synthesis of poly(methylidene-co-ethylidene) with a new secondary ylide monomer via C1 polymerization