ChemInform Abstract: An Efficient Synthesis of (Z)‐γ‐Fluoroallylphosphonates Using a Base‐Promoted Deconjugation of (E)‐γ‐Fluorovinylphosphonates, and Its Utility as Fluoroolefin‐Containing Building Block.

Abstract

An Efficient Synthesis of (Z)-γ-Fluoroallylphosphonates Using a Base-Promoted Deconjugation of (E)-γ-Fluorovinylphosphonates, and Its Utility as Fluoroolefin-Containing Building Block.-A facile threestep synthesis of γ-fluoroallylphosphonates (V) via a modified Pudovik reaction of α,β-unsaturated aldehydes with diethyl phosphite, DAST deoxyfluorination of the resulting hydroxyallylphosphonates (III), and finally, base-promoted double bond migration is described. Moreover, scope and limitation of this approach as well as some reactions of the title γ-fluoroallylphosphonates are studied. -(HAMMOND, GERALD B.; DEMENDONCA, DANIEL J.; J.