10374-51-3Relevant articles and documents
Asymmetric Bayer-Villiger oxidation of cyclobutanones
Lopp, Margus,Paju, Anne,Kanger, Tonis,Pehk, Tonis
, p. 7583 - 7586 (1996)
The asymmetric Baeyer-Villiger oxidation of racemic cyclobutanones 1, 2, and 3 and a prochiral cyclobutanone 4 under Sharpless oxidation conditions resulted in the enantiomeric lactones 5 ee 34%, 6 ee 53%, 7 ee 75% and 8 40% ee respectively.
Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenols using a water-soluble radical initiator in water. A facile synthesis of γ- lactones
Yorimitsu, Hideki,Wakabayashi, Katsuyu,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 519 - 522 (1999)
Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4'-azobis(4- cyanopentanoic acid), provided γ-(4-hydroxybutyl)-γ-lactone in 95% yield. The use of 2-iodoacetic acid in place of
THE TRANSFORMATION OF ALKENES INTO γ-LACTONES USING α-IODOESTERS
Kraus, George A.,Landgrebe, Kevin
, p. 3939 - 3942 (1984)
Iodostannyl esters react with alkenes in the presence of AIBN to afford γ-lactones.
DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES : V - EPOXY-2,3 PROPANATION DES ACIDES ET DERIVES PAR THERMOLYSE DU PEROXYDE D'ALLYLE ET DE t-BUTYLE
Montaudon, E.,Rakotomanana, F.,Maillard, B.
, p. 2727 - 2736 (1985)
The thermolysis of the allyl t-butylperoxide has been performed in esters, acids, anhydrides, nitriles and amides.Only esters and acetonitrile have been 2,3-epoxy propanated.With acids, the reaction product is the alkanoate of the hydroxymethyl-γ-butyrolactone corresponding to the cyclization of the expected epoxyacid and it is isolated with a good yield; the same compound is obtained putting the anhydride in place of the acid.
Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: Facile synthesis of γ-lactones
Yorimitsu,Wakabayashi,Shinokubo,Oshima
, p. 1963 - 1970 (2001)
Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis 4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.
Synthesis of functionalized γ-and δ-lactones via polymer-bound epoxides
Le Hetet, Claire,David, Michelle,Carreaux, Francois,Carboni, Bertrand,Sauleau, Armelle
, p. 5153 - 5156 (1997)
Solid phase synthesis of epoxides from alkenoic acids followed by ring-opening reactions with sodium azide or thiophenols and subsequent cleavage from the polymeric support afford γ- and δ-lactones in good yields and high purity.
Heterogeneous Permanganate Oxidation of 1,5-Dienes: A Novel Synthesis of 5-Substituted Butanolides
Baskaran, Sundarababu,Islam, Imadul,Vankar, Padma S.,Chandrasekaran, Srinivasan
, p. 626 - 627 (1992)
In the presence of a catalytic amount of water, 1,5-dienes undergo novel and unusual oxidation with potassium permanganate-copper sulfate in dichloromethane to give substituted butanolides in good yields under very mild conditions.
Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass
Deng, Weiping,Yan, Longfei,Wang, Binju,Zhang, Qihui,Song, Haiyan,Wang, Shanshan,Zhang, Qinghong,Wang, Ye
, p. 4712 - 4719 (2021)
Green synthesis of adipic acid from renewable biomass is a very attractive goal of sustainable chemistry. Herein, we report efficient catalysts for a two-step transformation of cellulose-derived glucose into adipic acid via glucaric acid. Carbon nanotube-supported platinum nanoparticles are found to work efficiently for the oxidation of glucose to glucaric acid. An activated carbon-supported bifunctional catalyst composed of rhenium oxide and palladium is discovered to be powerful for the removal of four hydroxyl groups in glucaric acid, affording adipic acid with a 99 % yield. Rhenium oxide functions for the deoxygenation but is less efficient for four hydroxyl group removal. The co-presence of palladium not only catalyzes the hydrogenation of olefin intermediates but also synergistically facilitates the deoxygenation. This work presents a green route for adipic acid synthesis and offers a bifunctional-catalysis strategy for efficient deoxygenation.
Epoxidation of alkenes bearing a carboxylic acid group by iron complexes of the tetradentate ligand N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1, 2-diaminoethane and its derivatives
Morris, Lilliana S.,Girouard, Michael P.,Everhart, Matthew H.,McClain, William E.,Van Paridon, John A.,Pike, Robert D.,Goh, Christopher
, p. 149 - 159 (2014)
The addition of carboxylic acids enhances the rate and selectivity of alkene oxidations catalyzed by [(bpmen)Fe(OTf)2] (bpmen = N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-diaminoethane). The syntheses and characterizations of four derivatives of this iron complex with varying substitutions on the pyridine ring and with a substituted piperazine backbone are reported. These [(L)Fe(OTf)2] complexes and [(bpmen)Fe(OTf)2] are employed as catalysts for the oxidation of alkenes bearing a carboxylic acid functional group, namely oleic acid, undecylenic acid, 5-hexenoic acid and 4-pentenoic acid, with hydrogen peroxide as the oxidant. Comparisons with the analogous ester substrates demonstrate the beneficial impact of the acid functional group on conversion and selectivity when using [(bpmen)Fe(OTf)2] as a catalyst. For the oleic and undecylenic acids, epoxide product is formed with moderate to high conversions and high selectivities. Under the conditions employed, 4-pentenoic acid is oxidized to a γ-lactone, most likely via the epoxide intermediate, and 5-hexenoic acid to a mixture of epoxide and δ-lactone. Of the iron complexes with bpmen derivatives as ligands, only the N,N′-dimethyl-N, N′-bis(5-chloropyridin-2-ylmethyl)-1,2-diaminoethane variant shows appreciable activity. The effect of solvent choice is also investigated.
Method for preparing 5-hydroxymethyldihydrofuran-2-one by taking furfural as raw material
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Paragraph 0022-0027, (2020/07/02)
The invention discloses a method for preparing 5-hydroxymethyldihydrofuran-2-one by using furfural as a raw material, and relates to a preparation method of an organic chemical raw material. The method is as follows: furfural is used as a raw material, ethanol is used as a solvent, a Raney nickel catalyst is used, and tetrahydrofurfuryl alcohol is prepared by catalytic hydrogenation reduction; gamma-Al2O3 is taken as a carrier, cerium nitrate and silver nitrate are taken as raw materials, and an Ag/CeO2/Gamma-Al2O3 catalyst is prepared by adopting an impregnation method, a roasting method anda natural cooling method; and the prepared tetrahydrofurfuryl alcohol is used as a raw material, the prepared Ag/CeO2/gamma-Al2O3 catalyst is adopted, and oxygen is introduced for a reaction to obtain5-hydroxymethyl dihydrofuran-2-one. The method is beneficial to improving the product selectivity; the catalyst is prepared by adopting a dipping-roasting method, the method is simple, the dispersityof active metal elements is good, and the product selectivity is high; and the product 5-hydroxymethyldihydrofuran-2-one has hydroxyl, furan ring and keto functional groups, is a raw material for synthesizing a plurality of antiviral, anticancer and anti-AIDS medicines, and has the advantages of high added value, high economic benefit and high social benefit.
