Oxidative Substitution Reactions of Organostannyl Compounds with Lead Tetraacetate. A Convenient Route to 5-Alkylidene-2(5H)-furanones

Article abstract of DOI:10.1246/bcsj.65.2366

5-Substituted 2-tributylstannylfurans which were synthesized by the reaction of corresponding 5-substituted 2-lithiofurans with tribitylstannyl chloride, were treated with two equimolar amounts of lead tetraacetate at room temperature to give corresponding 5-substituted 5-acetoxy-2(5H)-furanones in good yields.The 5-acetoxy-2(5H)-furanone was heated at 80 deg C in acetic acid-acetic anhydride containing a catalytic amount of concentrated sulfuric acid to give 5-alkylidene-2(5H)-furanone in moderate yield.