Английская Википедия:5-Hydroxy-2(5H)-furanone

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5-Hydroxy-2(5H)-furanone is a furanone derived from oxidation of furfural using singlet oxygen.[1][2] This oxidation is carried out generally in methanol or ethanol with a sensitizer like methylene blue or Rose bengal. The mechanism of this reaction is depicted as below.

Файл:Furfural-oxidation.png


Uses

5-Hydroxy-2(5H)-furanone is a potent pesticide[1] and a four carbon building block for various heterocycles.[3][4]

Chemical properties

5-Hydroxy-2(5H)-furanone exists in chemical equilibrium with its isomer, cis-β-formylacrylic acid, in ring-chain tautomerism:[5]

Файл:Tautomer of 5-Hydroxy-2(5H)-furanone.PNG

Under some conditions the compound will isomerize into succinic anhydride. Upon heating in strongly basic solution (pH > 9) this isomer will hydrate to succinic acid.[5]

See also

References