Advertisement
  • Open Access

Mechanism of the Phospha-Wittig–Horner Reaction

Authors


  • The Swedish Research Council, the Göran Gustafsson Foundation, COST action 0802 PhoSciNet, and Uppsala University (U3MEC molecular electronics priority initiative) is greatly acknowledged for financial support. A.O. would like to thank the Austrian Science fund (FWF) for an Erwin Schrödinger fellowship (J 3193-N17), Y.V.S. the Swedish Institute for a scholarship in the Visby Program (382/00386/2012).

Abstract

original image

Doing the phosphate dance: The phospha-Wittig–Horner reaction proceeds through stepwise P[BOND]P cleavage of an oxadiphosphetane intermediate, followed by a [2,3]-sigmatropic rearrangement that paves the way for the final E2 elimination to form 1-phosphaallenes. The mechanism is thus greatly different to that of its carbon analogue, that is, the Horner–Wadsworth–Emmons reaction.

Ancillary