Russian Journal of General Chemistry

, Volume 87, Issue 1, pp 50–59 | Cite as

Synthesis of 3-(furyl)acrylates containing several phosphonate groups

Article

Abstract

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.

Keywords

furoyl phosphonates Wittig reaction resonance-stabilized phosphoranes furylacrylates cis/trans isomerism 

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia

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