Journal of Organic Chemistry p. 3807 - 3810 (1985)
Update date:2022-08-03
Topics:
Newkome, George R.
Kiefer, Garry E.
Matsumura, Noboru
Puckett, Wallace E.
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.
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Doi:10.1016/0040-4020(62)80005-2
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