
%0 Journal Article
%A Doyle, IR 
%A Massy-Westropp, RA 
%T The synthesis, isomerization and stability of some enol-lactones
%J Australian Journal of Chemistry
%D 1982/09/01
%V 35
%N 9
%P 1903-1911
%K 
%R https://doi.org/10.1071/CH9821903
%U https://www.publish.csiro.au/paper/CH9821903 
%X The photoisomerization of enol-lactones is described. Thermal decomposition of (E) and (Z) ethyl 3-oxo-1,3,3a&#946;,4&#945;,7&#945;,7a&#946;-hexahydro-4,7-methanoisobenzofran-1-yideneacetates provides a good route to (E) and (Z) ethyl 5-oxo-2,5-dihydrofuran-2-ylideneacetates. Other examples of this retro-Diels-Alder reaction are reported. The relative stabilities of (E) and (Z) enol-lactones from the Wittig reaction between substituted succinic anhydrides and ethoxycarbonylmethylenetriphenylphosphorane have been determined. These Wittig reactions are under kinetic control. 
