title: Ugi reactions with CO2 : access to functionalized polyurethanes, polycarbonates, polyamides, and polyhydantoins.
abstract: A novel strategy for the incorporation of carbon dioxide into polymers is introduced. For this purpose, the Ugi five-component condensation (Ugi-5CC) of an alcohol, CO2 , an amine, an aldehyde, and an isocyanide is used to obtain step-growth monomers. Polymerization via thiol-ene reaction or polycondensation with diphenyl carbonate gives diversely substituted polyurethanes or alternating polyurethane-polycarbonates, respectively. Furthermore, the application of 1,12-diaminododecane and 1,6-diisocyanohexane as bifunctional components in the Ugi-5CC directly results in the corresponding polyamide bearing methyl carbamate side chains (M¯n = 19 850 g mol(-1) ). The latter polymer is further converted into the corresponding polyhydantoin in a highly straightforward fashion.
authors.affiliation: Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Ansgar
authors.initials: A
authors.lastname: Sehlinger
authors.forename: Rebekka
authors.initials: R
authors.lastname: Schneider
authors.forename: Michael A R
authors.initials: MA
authors.lastname: Meier
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry; D003959:Diamines / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D006827:Hydantoins / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D009757:Nylons / Q000737:chemistry*; D011076:Polycarboxylate Cement / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011140:Polyurethanes / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D003486:Cyanides; D003959:Diamines; D006586:Hexanes; D006827:Hydantoins; D009757:Nylons; D011076:Polycarboxylate Cement; D011108:Polymers; D011140:Polyurethanes; D002245:Carbon Dioxide; C005506:polycarbonate; C016417:1,12-dodecamethylenediamine
keywords: Ugi five-component condensation; carbon dioxide; multicomponent reactions; polyurethanes; poly­hydantoins