As shown in table 3, diethylene glycol (1e) gave 1,4-dioxane (3e) in 85% yield, and triethylene glycol (1f) under these conditions gave 1,4-dioxane (3e) in 89% yield. E-mail: All authors gave final approval for publication. or in a thesis or dissertation provided that the correct acknowledgement is given organoselenium reagents; contained in this article in third party publications If you are the author of this article you do not need to formally request permission Go to our The present cyclization could proceed at room temperature to produce 5–7 membered cyclic ethers in good to excellent yields. Numerous natural and biologically active products have been prepared by using this synthetic route. Stirring and heating at this temperature were continued until the distillation stopped (8 h). The efficiencies of various HPAs catalysts used in the synthesis of THF. Next, the optimum reaction conditions were used in the synthesis of cyclic ethers by cyclodehydration of 1,n-diols catalysed by catalyst 2a . the whole article in a third party publication with the exception of reproduction Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication of different cyclic ethers units, which are the key structural units of many natural products. Next, the optimum reaction conditions were used in the synthesis of cyclic ethers by cyclodehydration of 1,n-diols catalysed by catalyst 2a (table 3). Information about reproducing material from RSC articles with different licences Instructions for using Copyright Clearance Center page for details. This work was supported by the National Natural Science Foundation of China (31501683) and the Special Fund for Supervision of Quality and Safety of Agricultural Products (Risk Assessment) from the Chinese Ministry of Agriculture (GJFP 2017011). Intramolecular etherification of 1,3-diols was investigated using iodine as a catalyst under solvent-free conditions. These were significantly higher yields of cyclic ether 3e from diethylene glycol (1e) and triethylene glycol (1f) than previously obtained using other catalyst systems [34–38]. THF (664.60 g, 9.23 mol; 92.3% yield) was obtained after drying over molecular sieves and filtering. The catalytic activities decreased in the following order: 2a (H3PW12O40) > 2c (H4SiW12O40) > 2b (H3PMo12O40) > 2d (H4SiMo12O40). “The Shortest (Four-step) Total Synthesis of Eight-membered Cyclic Ether ()- and (-)-cis-Lauthisan”G. Catalysts 2a and 2c provided higher yields than the other catalysts. aReaction conditions: butane-1,4-diol (200 mmol). Cyclodehydration of heptane-1,7-diol (1k) to form 3h did not occur because the catalyst was too far from the diol group to play a direct role. 1H NMR (300 MHz; CDCl3) δ: 3.60 (4H, t, J = 5.0 Hz), 1.49–1.64 (6H, m). theallyl-phenolethers.Claisen^hasprovedthatpyridinehydro- chlorideconverts them quantitatively into methyl coumaranee.The presentinvestigationproves that para-bromomethylene coumarane, S. Asai, M. Kato, Y. Monguchi, H. Sajiki and Y. Sawama, Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Instructions for using Copyright Clearance Center page. Table 1.The efficiencies of various HPAs catalysts used in the synthesis of THF. Based upon the above optimum reaction conditions, amplification experiments were performed. Optimization of the synthesis of THF catalysed by H, Anticorrosive assay-guided isolation of active phytoconstituents from, Identification of potent chromone embedded [1,2,3]-triazoles as novel antitubercular agents, A practical and chemoselective ammonia-free birch reduction, A one-pot tandem oxidation–reduction protocol for the synthesis of cyclic ethers from their diols, Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural, One-pot regio- and stereoselective cyclization of 1, 2, n-triols, Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids, Iron-catalyzed ring-closing depolymerization of poly (tetrahydrofuran), Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups, Kinetic analysis of aqueous-phase cyclodehydration of 1, 4-butanediol and erythritol over a layered niobium molybdate solid acid, Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: acetylation of nopol and terpenic alcohols, Use of solid catalysts in Friedel–Crafts acylation reactions, Recent advances in polyoxometalate-catalyzed reactions, Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions, Electrochemical investigation of photooxidation processes promoted by sulfo-polyoxometalates: coupling of photochemical and electrochemical processes into an effective catalytic cycle, Selective catalytic dehydration of furfuryl alcohol to 2,2′-difurfuryl ether using a polyoxometalate catalyst, Preparation, characterization and catalytic application for the synthesis of tetrahydrofuran, Dehydration of methanol to dimethyl ether over heteropoly acid catalysts: the relationship between reaction rate and catalyst acid strength, Heteropolyacid-based catalysis: Dawson acid for MTBE synthesis in gas phase, Solvent-free catalytic preparation of 1, 1-diacetates from aldehydes using a Wells–Dawson acid (H, A solvent-free synthesis of coumarins using a Wells–Dawson heteropoly acid as catalyst, Facile preparation of symmetrical and unsymmetrical ethers from their corresponding alcohols catalyzed by aluminumdodecatangstophosphate (AlPW, An efficient and chemoselective method for protection of thiols catalyzed by aluminumdodecatungstophosphate (AlPW, Cerium (IV) ammonium nitrate a versatile single-electron oxidant, Production of tetrahydrofuran by dehydration of 1, 4-butanediol using Amberlyst-15: batch kinetics and batch reactive distillation, One-pot transformation of levulinic acid to 2-methyltetrahydrofuran catalyzed by Pt–Mo/H-β in water, Rapidly responsive and highly selective fluorescent probe for bisulfite detection in food, Highly selective and rapidly responsive fluorescent probe for hydrogen sulfide detection in wine, Facile method for the synthesis of 2, 3-dihydroquinazolin-4(1H)-ones catalyzed by SiO, Metal (IV) phosphates as solid acid catalysts for selective cyclodehydration of 1,n-diols, Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate, Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic S, Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols, Synthesis of common-sized heterocyclic compounds by intramolecular cyclization over halide cluster catalysts, https://dx.doi.org/10.6084/m9.figshare.c.4226378, http://creativecommons.org/licenses/by/4.0/, doi:10.4028/www.scientific.net/AMR.838-841.2322. A yield of 98% was obtained under optimum conditions of 0.1 mol% catalyst loading at 100°C for 3 h reaction. 62 122 18.8: Ring-Opening Reactions of Epoxides Acid-catalyzed epoxide opening: protonation of the epoxide Authors contributing to RSC publications (journal articles, books or book chapters) 13C NMR (75 MHz; CDCl3) δ: 68.6, 26.7, 23.3. The metals of the HPA catalysts were the selected focus because they are the active sites in the acid-catalysed reactions [18,19]. 1H NMR (300 MHz; CDCl3) δ: 3.58–3.62 (4H, m), 1.67–1.76 (4H, m). Similarly, polyethylene glycol 200 (1g) gave 1,4-dioxane (3e) in an excellent yield of 86% (table 3). Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their stereochemistries. * In all cases the Ref. Accordingly, a series of HPA catalysts were prepared, as summarized in table 1, and a set of standard experimental conditions employed (100°C for 3 h) to assess the relative utility of the synthetic catalysts. Pressing the buy now button more than once may result in multiple purchases, Authors: M. Bugarcic, Zorica; D. Kostic, Marina; M. Divac, Vera, Source: Current Organic Chemistry, Volume 20, Number 7, 2016, pp. Compounds 3a–3g (table 3) were all synthesized using the same approach according to the synthetic method described for 3a in ‘Material and methods’. If you are the author of this article you still need to obtain permission to reproduce

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