title: Diels-Alder Reactions of Furans with Itaconic Anhydride: Overcoming Unfavorable Thermodynamics.
abstract: Unfavorable thermodynamics often render furans reluctant to engage in high-yielding Diels-Alder (DA) cycloaddition reactions. Here, we report the highly efficient conversion of the biosourced reactants itaconic anhydride (IA) and furfuryl alcohol (FA) to a single DA adduct. The free energy advantages provided by anhydride ring opening and crystal lattice energy of the product overcome the loss of aromaticity of the furanoid diene. Detailed (1)H NMR studies provided valuable insights about relevant kinetic and thermodynamic features.
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Ashok D
authors.initials: AD
authors.lastname: Pehere
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Shu
authors.initials: S
authors.lastname: Xu
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Severin K
authors.initials: SK
authors.lastname: Thompson
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Marc A
authors.initials: MA
authors.lastname: Hillmyer
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Hoye
mesh_terms: D000812:Anhydrides / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D005663:Furans / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis*; D013386:Succinates / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D000812:Anhydrides; D005663:Furans; D007783:Lactones; D013386:Succinates; C005229:itaconic acid