- Dynamic Trapping as a Selective Route to Renewable Phthalide from Biomass-Derived Furfuryl Alcohol
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A novel route for the production of the versatile chemical building block phthalide from biorenewable furfuryl alcohol and acrylate esters is presented. Two challenges that limit sustainable aromatics production via Diels–Alder (DA) aromatisation—an unfavourable equilibrium position and undesired regioselectivity when using asymmetric addends—were addressed using a dynamic kinetic trapping strategy. Activated acrylates were used to speed up the forward and reverse DA reactions, allowing for one of the four DA adducts to undergo a selective intramolecular lactonisation reaction in the presence of a weak base. The adduct is removed from the equilibrium pool, pulling the system completely to the product with a fixed, desired regiochemistry. A single 1,2-regioisomeric lactone product was formed in up to 86 % yield and the acrylate activating agent liberated for reuse. The lactone was aromatised to give phthalide in almost quantitative yield in the presence of Ac2O and a catalytic amount of strong acid, or in 79 % using only catalytic acid.
- Lancefield, Christopher S.,F?lker, Bart,Cioc, Razvan C.,Stanciakova, Katarina,Bulo, Rosa E.,Lutz, Martin,Crockatt, Marc,Bruijnincx, Pieter C. A.
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- AMMONIUM SALTS IN ALKYLATION REACTIONS. 34. SYNTHESIS AND INTRAMOLECULAR CYCLIZATION OF UNSATURATED ESTERS WITH A FURFURYL GROUP
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Unsaturated esters of furfuryl alcohol were synthesized by interphase catalysis.The intramolecular thermal cyclization of the synthesized compound was studied.
- Torosyan, G. O.,Akopyan, A. A.,Torosyan, A. T.,Babayan, A. T.
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- REVERSIBLE POLYMERIC GELATION FOR OILFIELD APPLICATIONS
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This invention relates to the synthesis and use in oilfield applications of copolymers which can undergo the Diels-Alder reaction to form a gel. Under appropriate conditions, the retro Diels-Alder reaction can take place to provide for decreasing the viscosity of the aforementioned gel.
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- Process for directly converting an aldehyde into an ethylene ester
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The invention concerns a process for directly converting an aldehyde into an ethylene ester, of the type wherein the aldehyde is placed in the presence of an alkaline carbonate or bicarbonate and of a phosphonate into a solvent with an alcohol function. In the invention, an ethyl phosphonate or a methyl phosphonate is used and the solvent is an alcohol or a polyol including a hydrocarbon radical other than ethyl or methyl, this radical being that of the ethylenic ester to be produced. The process of the invention makes it possible to directly convert furan aldehyde or tetrahydrofuran aldehyde to produce an ethylenic ester with a furan ring or a tetrahydrofuran ring.
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