Reactions of ethylidene diacetate: Formation of N-vinylamide precursors ethylidene bisacetamide and ethylidene bisformamide

Article abstract of DOI:10.1016/S0040-4039(97)01089-7

Ethylidene diacetate (EDA) reacts with formamide or acetamide under stoichiometric base or catalytic Lewis acid conditions to afford the corresponding ethylidene bisamides and N-vinylamides. Sn(OAc)₂ afforded an overall 82.6% selectivity to the desired acetamide derivatives. Sn(OAc)₂ and Zn(OAc)₂ facilitate amide attack at the tertiary carbon of EDA.