Cross-metathesis (CM) has been shown for the first time to be a useful method for the synthesis of side-chain functionalized polysaccharide derivatives. Commercially available cellulose esters were acylated by 10-undecenoyl chloride, providing esters with olefin-terminated side chains. Subsequent CM reactions of these terminal olefin moieties with a variety of CM partners including acrylic acid, acrylates, acrylamides, allylic alcohols, N-vinylpyrrolidone were performed. Complete conversion to discrete, soluble CM products was achieved in acrylic acid by using Hoveyda-Grubbs' 2ndgeneration catalyst and an excess of cross-metathesis partner. Polydispersity index (PDI) data and NMR spectra strongly indicated that intra- and intermolecular self-metathesis (SM) was successfully suppressed. Conversion of terminally-olefinic cellulose esters to a variety of CM products varied from 0% to 100%, mainly depending on olefin species and solvent. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/240nm/uploads/32283_acs2010fig2.jpg' alt='' />

Olefin cross-metathesis as a source of novel polysaccharide derivatives

247th National Meeting (2014)

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