Wittig-Horner Reaction in Heterogenous Media: V¹. An Efficient Synthesis of Alkene-Phosphonates and αL-Hydroxymethyl-α-Vinyl Phosphonate in Water in the Presence of Potassium Carbonate

Abstract

Among the various ways of carrying out the Wittig-Horner reaction, the application of the two-phase system using 50% aqueous NaOH as base with (or) without a phase-transfer catalyst has been a subject of increasing interest over the past few We have shown^l,4 that the use of less basic heterogenous media, including aqueous K₂C0₃ or KHC0₃ or the same bases in Toluene or THF enabled these reactions to be carried out with high yields even with base sens it i ve carbony I compounds. These react ions, that do not need phase transfer catalyst proceed by displacement of acido-basic equilibria by the coupling of the anion 2 of the phosphonate 1 with the electrophilic carbonyl compound 3.