1967 Volume 40 Issue 9 Pages 2135-2139
The reaction of either N-(p-chlorophenyl)diphenylketenimine or N-(p-chlorophenyl)diphenylacetimidoyl chloride with ethyl cyanoacetate gave the identical α, β-unsaturated ester. Whilst the reaction of the ketenimine with diethyl malonate yielded β, γ-unsaturated diester, the isomeric α, β-unsaturated diester was obtained by the reaction of the imidoyl chloride with the malonate. These remarkable different phenomena could be ascribed to the difference in bulk between cyano and carbethoxy groups. The structures of these products were discussed on the basis of the infrared and ultraviolet spectroscopic data and the reaction mechanisms were proposed. Additionally, the pyrolysis of the products was studied and the β, γ-unsaturated diester was found to give quinolin-4-one together with an α-naphthol derivative under elimination of ethanol, whilst only quinolin-4-one was isolated on the pyrolysis of the isomeric α, β-unsaturated diester.
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