Tetrahedron letters

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

JJ Rabasco, FJ Waller

Index: Rabasco, John J.; Waller, Francis J. Tetrahedron Letters, 1997 , vol. 38, # 28 p. 4953 - 4956

Full Text: HTML

Citation Number: 0

Abstract

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.