
%0 Journal Article
%A Babidge, PJ 
%A Massy-Westropp, RA 
%T The synthesis of 5-Alkylidenefuran-2(5H)-ones
%J Australian Journal of Chemistry
%D 1981/08/01
%V 34
%N 8
%P 1745-1756
%K 
%R https://doi.org/10.1071/CH9811745
%U https://www.publish.csiro.au/paper/CH9811745 
%X 5-Alkylidenefuran-2(5H)-ones can be synthesized efficiently from S- methyl 5-oxo-2,5-dihydro-furanylidenealkanethioates by treatment with Raney nickel. The ylidenealkanethioates are prepared from the Wittig reactions between cyclic anhydrides and (methylthio)carbonylmethylenetriphenyl-phosphorane or its alkylated derivative. The decarbonylation-desulfurization process proceeds largely with retention of configuration about the double bond. It is considered that the reaction proceeds by loss of carbon monoxide to give a thioenol ether which is subsequently hydrogenolysed to the 5- alkylidenefuran-2(5H)-one. 
