The synthesis of 5-Alkylidenefuran-2(5H)-ones
- 1 January 1981
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 34 (8) , 1745-1756
- https://doi.org/10.1071/ch9811745
Abstract
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.Keywords
This publication has 1 reference indexed in Scilit:
- Synthetic approaches towards 4-ylidenebutenolides and 4-ylidenetetronic acids. Regioselective nucleophilic additions to unsymmetrically substituted maleic anhydridesJournal of the Chemical Society, Perkin Transactions 1, 1979