title: Renewable rigid diamines: efficient, stereospecific synthesis of high purity isohexide diamines.
abstract: We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide-a tricyclic adduct-was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.
authors: Food & Biobased Research, Wageningen University & Research Centre, Wageningen, The Netherlands.
authors: Shanmugam
authors: S
authors: Thiyagarajan
authors: Linda
authors: L
authors: Gootjes
authors: Willem
authors: W
authors: Vogelzang
authors: Jacco
authors: J
authors: van Haveren
authors: Martin
authors: M
authors: Lutz
authors: Daan S
authors: DS
authors: van Es
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003247:Conservation of Natural Resources; D003959:Diamines / Q000138:chemical synthesis*; D007547:Isosorbide / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: C502182:1,4-3,6-dianhydromannitol; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003959:Diamines; D011108:Polymers; D007547:Isosorbide