O-vinylacetoxime as a hydrogen bond acceptor

According to quantum chemical calculations (B3LYP/6-311G*) and IR spectroscopy the basicity of oxygen atom of O-vinylacetoxime is substantially lower than that of O-ethylacetoxime and is comparable to the basicity of phenyl vinyl and diphenyl ethers. In CCl₄ solution, O-vinylacetoxime gives H-complexes wit methanol by formation of N···HO bonds. With phenol and trifluoroacetic acid under these conditions it enters in the reaction of electrophilic addition. O-Ethylacetoxime in inert media forms with methanol and phenol two types of H-complexes with the N···HO or O···HO bonds.