88517-51-5Relevant articles and documents
Niobium(V) chloride as catalyst in diels-alder reaction of furan ring
Santos, Deborah A. Dos,Rodrigues, Ludmila R.,Arpini, Bruno H.,Lacerda Jr., Valdemar,Greco, Sandro J.,Santos, Reginaldo B. Dos,Neto, A?lvaro C.,Roma?oa, Wanderson,De Castro, Eustaquio V.R.
, p. 882 - 886 (2014)
According to the relevant literature, the Diels-Alder reaction of furan without a catalyst can last several weeks and shows a low yield due to the diene's low reactivity. The use of Lewis acid catalysts or high pressures is described as an effective method for improving the reaction yields. This paper describes our recent study on the use of niobium pentachloride as the catalyst in Diels-Alder reactions between furan and several reactive dienophiles, among which methyl acrylate showed good yields, especially at lower temperatures. Other dienophiles have shown lower yields because of problems such as byproduct formation and the high reversibility of the reaction.
Diels-Alder and Dehydration Reactions of Biomass-Derived Furan and Acrylic Acid for the Synthesis of Benzoic Acid
Mahmoud, Eyas,Yu, Jingye,Gorte, Raymond J.,Lobo, Raul F.
, p. 6946 - 6955 (2015/11/23)
Routes to benzoic acid starting from furan-obtained from hemicellulose in high yield-and methyl acrylate are reported. These routes involve Diels-Alder and dehydration reactions of furan and acrylic acid (or methyl acrylate) in a two-step reaction protocol that minimizes side reactions. The Diels-Alder reaction of furan and methyl acrylate (or acrylic acid) was run at 298 K and was catalyzed by Lewis acidic (Hf-, Zr-, and Sn-Beta) zeolite catalysts, and achieving a high turnover frequency (～2 h-1) and no side reactions were observed. The oxanorbornene product was dehydrated at low temperatures (298 to 353 K) in mixtures of methanesulfonic acid and acetic anhydride in 96% yield. This is compared to an only 1.7% yield of methyl benzoate obtained for the dehydration of the oxanorbornene in neat methanesulfonic acid. The effect of oxanorbornene concentration and stereochemistry was found not to decrease the yield of aromatics, while dehydration of the carboxylic acid form of the oxanorbornene led to a decrease in selectivity to 43% at complete conversion in mixtures of methanesulfonic acid and acetic anhydride. This reaction sequence could be an important entry point for selectively directing high-yield, hemicellulose-derived furans to aromatic products used in the existing chemical process industry.
Norbornenes in inverse electron-demand diels-alder reactions
Vrabel, Milan,Koelle, Patrick,Brunner, Korbinian M.,Gattner, Michael J.,Lopez-Carrillo, Veronica,De Vivie-Riedle, Regina,Carell, Thomas
supporting information, p. 13309 - 13312 (2013/10/08)
Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum-chemical calculations were used to rationalize and support the observed experimental data. Copyright
