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Vinylogy concept

Firstly introduced by R. C. Fuson in 1935, the “Principle of Vinylogy” states that a given functional group within a molecule may relay its function (i.e. its electronic properties) to a distant point in the molecule provided that interposed conjugated unsaturated linkages are present. As an example, γ-enolization of α,β-unsaturated carbonyl compounds provides ambident C-nucleophiles where the conventional “normal” C-α nucleophilicity may be usurped by that of the distant, vinylogous C-γ carbon atom. Extending this concept, a conjugated polyenolate may be regarded as a multi-site C-nucleophile on the alternating α, γ, ε, ..., ω carbon sites. The synthesis of such pluripotent substrates and their use in chemo/regio/stereocontrolled synthesis is a formidable challenge in contemporary organic synthesis.

Pubblicato Wednesday, 11 January, 2017 - 21:30 | ultima modifica Wednesday, 11 January, 2017 - 21:31