Synthesis of Vinyl Derivatives of Phenanthroline and Bipyridine

Article abstract of DOI:10.1021/jo00220a025

A new series od bipyridine and phenanthroline vinyl heterocycle has been synthesized via Wittig-Horner reaction.These products arise from the enhanced anion stabilization present in the heterocyclic phosphonate which facilitates β-hydroxy elimination of the intermediate condensation product to generate a vinyl phosphonate.A vinyl phosphonates obtained under these conditions in aqueous methanol undergo facile nucleophilic addition of methoxide with subsequent regeneration of the olefin.In addition, 6,6'-divinyl-2,2'-bipyridine was synthesized under standard Wittig reaction conditions from the corresponding dialdehyde.The 1H NMR spectral data of these compounds ere discussed in detail.