Novel unsaturated ethers were synthesised in good yields starting from sucrose, using a two-step mild and efficient procedure based on the Gassman method, which consists in forming a vinyl group by the elimination of ethanol from mixed acetals with trimethylsilyl trifluoromethanesulfonate in the presence of alkyl amines. Mixed acetals are readily obtained from the corresponding alcohols and ethyl vinyl ether, using an acidic catalyst. Conventional etherification involving a primary halide was also examined. The monomers thus obtained were successfully polymerised by a free radical mechanism, yielding unbranched linear and soluble polymers with pending sucrose moieties, and some of their physical properties were determined.
|Publication status||Published - 1 Jan 2008|