Organo-catalyzed ring opening polymerization of a 1,4-dioxane-2,5-dione deriving from glutamic acid
The (3S)-[(benzyloxycarbonyl)ethyl]-1,4-dioxan-2,5-dione (BED) was prepared in four steps starting from glutamic acid and bromoacetyl bromide. According to X-ray diffraction analysis, the pendant functional group is located in equatorial position and points away from the six-membered ring. The organo-catalyzed ring-opening polymerization of BED was promoted with 4-dimethylaminopyridine (DMAP) and the combination of thiourea TUCy and (-)-sparteine. PolyBED samples of number-average molar mass Mn up to 36000 and narrow polydispersity (Mw/Mn 1H-13C HMBC 2D NMR experiment. The preparation of 1:1 adducts with n-pentanol confirmed that ring-opening of BED occurs almost indifferently on either of the endocyclic ester groups. Poly(α-hydroxyacids) featuring pendant carboxylic acids were finally obtained by acetylation of the terminal OH groups followed by hydrogenolysis.
Du Boullay, Olivier Thillaye,Saffon, Nathalie,Diehl, Jean-Pierre,Martin-Vaca, Blanca,Bourissou, Didier
p. 1921 - 1929
(2011/04/17)
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