Synthesis of 3-(furyl)acrylates containing several phosphonate groups
Isomeric (diethoxyphosphorylmethyl)furoyl phosphonates react with ethoxycarbonylmethylenetriphenylphosphorane to form 3-[(diethoxyphosphorylmethyl)fyryl]-3-(diethoxyphosphoryl)acrylates with trans-location of phosphonate and ester groups regardless of the structure of heterocyclic residue. 2,5-Bis(diethoxyphosphorylmethyl)-3-furoyl phosphonate and 4,5-bis(diethoxyphosphorylmethyl)-2-furoyl phosphonate prepared from the corresponding acid chlorides via the Arbuzov reaction behave analogously. The dependence of coupling costants J PP and J PC on the location of phosphorus-containing substituents in the furan ring of these compounds is analyzed.
Keywordsfuroyl phosphonates Wittig reaction resonance-stabilized phosphoranes furylacrylates cis/trans isomerism
Unable to display preview. Download preview PDF.