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Tetrahydrofuran

About: Tetrahydrofuran is a research topic. Over the lifetime, 11778 publications have been published within this topic receiving 158241 citations. The topic is also known as: diethylene oxide & 1,4-epoxybutane.


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Journal ArticleDOI
TL;DR: In this paper, a novel cosolvent based biomass pretreatment method called CELF (Cosolvent Enhanced Lignocellulosic Fractionation) which employs tetrahydrofuran (THF) in a single phase mixture with water, was found to be highly effective at solubilizing and extracting lignin from lignosic biomass and achieving high yields of fermentable sugars.

112 citations

Journal ArticleDOI
TL;DR: A series of single crystals of tetrakis as discussed by the authors have been prepared where the monoanion is a hexanuclear chalcohalide rhenium cluster and the neutral guest molecules are dimethylformamide (DMF) in 2a and 2b (triclinic modification), tetrahydrofuran (THF), and dioxane in 2d).
Abstract: A series of single crystals of tetrakis[3,4,3',4'-bis(ethylenedithio)-2,2',5,5'-tetrathiafulvalene] Re 6 Se 5 Cl 9 .-guest] (2a-d) have been prepared where the monoanion is a hexanuclear chalcohalide rhenium cluster and the neutral guest molecules are dimethylformamide (DMF) in 2a (monoclinic modification) and 2b (triclinic modification), tetrahydrofuran (THF) in 2c, and dioxane in 2d. All four compounds present the same basic structural organization in which conducting organic cation radical slabs are sandwichdn by inorganic cluster monoanion layers

112 citations

Journal ArticleDOI
Abstract: The rates of Bronsted-acid-catalyzed reactions of ethyl tert-butyl ether, tert-butanol, levoglucosan, 1,2-propanediol, fructose, cellobiose, and xylitol were measured in solvent mixtures of water with three polar aprotic cosolvents: γ-valerolactone; 1,4-dioxane; and tetrahydrofuran. As the water content of the solvent environment decreases, reactants with more hydroxyl groups have higher catalytic turnover rates for both hydrolysis and dehydration reactions. We present classical molecular dynamics simulations to explain these solvent effects in terms of three simulation-derived observables: (1) the extent of water enrichment in the local solvent domain of the reactant; (2) the average hydrogen bonding lifetime between water molecules and the reactant; and (3) the fraction of the reactant accessible surface area occupied by hydroxyl groups, all as a function of solvent composition. We develop a model, constituted by linear combinations of these three observables, that predicts experimentally determined rate constants as a function of solvent composition for the entire set of acid-catalyzed reactions.

112 citations

Journal ArticleDOI
TL;DR: In this paper, an aza-Payne rearrangement of N-activated 2-aziridinemethanols, synthesized in an optically active form, with potassium tert-butoxide (ButOK), potassium hydride (KH), or sodium hydrides (NaH) at near 0 °C in common aprotic solvents such as tetrahydrofuran (THF), toluene, or a mixed solvent of THF-HMPA followed by quenching at low temperature gives the corresponding epoxy sulfon
Abstract: An aza-Payne rearrangement of N-activated 2-aziridinemethanols, synthesized in an optically active form, with potassium tert-butoxide (ButOK), potassium hydride (KH), or sodium hydride (NaH) at near 0 °C in common aprotic solvents such as tetrahydrofuran (THF), toluene, or a mixed solvent of THF–HMPA followed by quenching at low temperature gives the corresponding epoxy sulfonamides in high yields. The anionic reaction intermediates, generated by treatment of 2-aziridinemethanols with a base, react readily in a one-pot manner with a variety of nucleophiles such as organocopper reagents, thiols, and trimethylsilyl cyanide to yield the optically active corresponding functionalized 1,2-amino alcohols in good yields. Upon exposure of 2,3-epoxy amines to an equimolar mixture of ButOK and BuLi (super base) in a mixed solvent of THF and n-hexane at –78 °C, the equilibrium lies exclusively toward the hydroxyaziridine forming direction.

111 citations

Journal ArticleDOI
TL;DR: The first catalytic method for the efficient conversion of epoxides to succinic anhydrides via one-pot doublecarbonylation is reported, which reveals that the two carbonylation stages are sequential and non-overlapping, such that epoxide carbonylated goes to completion before any of the intermediate beta-lactone is consumed.
Abstract: The first catalytic method for the efficient conversion of epoxides to succinic anhydrides via one-pot double carbonylation is reported. This reaction occurs in two stages: first, the epoxide is carbonylated to a β-lactone, and then the β-lactone is subsequently carbonylated to a succinic anhydride. This reaction is made possible by the bimetallic catalyst [(ClTPP)Al(THF)2]+[Co(CO)4]- (1; ClTPP = meso-tetra(4-chlorophenyl)porphyrinato; THF = tetrahydrofuran), which is highly active and selective for both epoxide and lactone carbonylation, and by the identification of a solvent that facilitates both stages. The catalysis is compatible with substituted epoxides having aliphatic, aromatic, alkene, ether, ester, alcohol, nitrile, and amide functional groups. Disubstituted and enantiomerically pure anhydrides are synthesized from epoxides with excellent retention of stereochemical purity. The mechanism of epoxide double carbonylation with 1 was investigated by in situ IR spectroscopy, which reveals that the t...

111 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023194
2022382
2021124
2020154
2019193
2018218