949895-84-5Relevant articles and documents
Synthesis of polyoxazolines using glycerol carbonate derivative and end chains functionalization via carbonate and isocyanate routes
Giardi, Chloe,Lapinte, Vincent,Nielloud, Francoise,Devoisselle, Jean-Marie,Robin, Jean-Jacques
, p. 4027 - 4035 (2010)
We report the cationic ring-opening polymerization of 2-methyl-2-oxazoline (MOx) using bio-based initiator (GCTs). The functional initiator GCTs was prepared by tosylation of the corresponding alcohol: glycerol carbonate (GC). The termination stage of the polymerization was achieved in presence of KOH and the telechelic polyoxazoline carrying five-membered cyclic carbonate and oxazolium end groups (GC-POxium) was converted to ((HO) 2-POx-OH) carrying α-diol and ω-hydroxyl groups. End-functionalized polyoxazolines (HO)2-POx-OH with Mn ranging from 4200 to 8400 g mol-1 were synthesized. According to GPC results, the polymerizations of MOx using GCTs and other initiator coming from 1,2-isopropylidene-glycerol (Solk-Ts) were compared. On the basis of FTIR and NMR spectroscopies, the chemical modification of end chains of polyoxazolines was investigated by two alternative synthetic routes. The isocyanate route is a postpolymerization urethanization. The nucleophilic reactivity of the α-diol and ω-hydroxyl groups of (HO)2-POx-OH was studied with functional isocyanate (TESPI). In the carbonate route, the electrophilic reactivity of α- and ω-end groups of GC-POxium were explored with amine. It was demonstrated that during the termination stage of the polymerization in presence of aliylamine both urethane linker in α-end chain was synthesized and the ω-oxazolium group was converted into terminal amine. The carbonate route is an alternative to synthesize urethane without isocyanate.
A powerful aluminum catalyst for the synthesis of highly functional organic carbonates
Whiteoak, Christopher J.,Kielland, Nicola,Laserna, Victor,Escudero-Adán, Eduardo C.,Martin, Eddy,Kleij, Arjan W.
supporting information, p. 1228 - 1231 (2013/03/14)
An aluminum complex based on an amino triphenolate ligand scaffold shows unprecedented high activity (initial TOFs up to 36 000 h-1), broad substrate scope, and functional group tolerance in the formation of highly functional organic carbonates prepared from epoxides and CO2. The developed catalytic protocol is further characterized by low catalyst loadings and relative mild reaction conditions using a cheap, abundant, and nontoxic metal.
Valorization of glycerol 1,2-carbonate as a precursor for the development of new synthons in organic chemistry
Bensemhoun, Julia,Condon, Sylvie
, p. 2595 - 2599 (2013/02/23)
Conjugate addition reactions are efficiently performed by a very simple electrochemical method using nickel complexes as catalysts. In this paper, we reported a new method for the valorization of glycerol 1,2-carbonate. Firstly, we prepared the activated glycerol 1,2-carbonate derivatives (halogen or pseudo-halide derivatives), and secondly applied these halogen derivatives in coupling reactions by electrochemical methods with organic compounds and environment-friendly solvent (propylene carbonate). To our knowledge, this is the first report of creation of carbon-carbon bonds on the glycerol 1,2-carbonate and of the synthesis of these compounds.
