By-products: Alkenes from Furfural (Intro)

The Wittig reaction was discovered in 1954 by Georg Wittig, for which he was awarded the Nobel Prize in Chemistry in 1979 Functionalized alkenes and epoxydes Furfural chosen as a model molecule was in this way transformed quantitatively into 2-vinyl furane or into the corresponding functionalized alkenes in the presence of an hydroxide or a […]

08.09.2012

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Wittig Reaction: Furfural to Furfurylidene

The Wittig reaction was discovered in 1954 by Georg Wittig, for which he was awarded the Nobel Prize in Chemistry in 1979

Functionalized alkenes and epoxydes

transfert-solide-liquide--alcenes-fonctionnalises

Furfural chosen as a model molecule was in this way transformed quantitatively into 2-vinyl furane or into the corresponding functionalized alkenes in the presence of an hydroxide or a solid alkaline carbonate, of an organic phase constituted by the solvent of the considered reagents and traces of water of carefully quantified quantities. This reaction, generalized to all of the carbonyl function, works according to an original reaction processus which privileges, due to the specific solvatation of the intermediate species at the solid / liquid interface, a preferential orientation to Z or E alkene. It also allows the transformation of phenolic aldehydes into the corresponding alkenes and particularly the first direct synthesis from p-hydroxybenzaldehyde, from 2-vinyl phenol or from p-hydroxystyrene, monomer of big interest in macromolecular chemistry.

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