Novel reactions of carbon suboxide. Part 8. Kinetic study of the reaction with substituted 2-hydroxybenzaldehyde oximes

L Bonsignore, G Loy, M Secci, S Cabiddu…

Index: Bonsignore, Leonardo; Loy, Giuseppe; Secci, Mario; Cabiddu, Salvatore Synthesis, 1984 , # 3 p. 266

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Citation Number: 6

Abstract

The kinetics of the reaction of carbon suboxide with aryl-substituted 2-hydroxybenzaldehyde oximes to give coumarin derivatives have been studies. A Hammett plot gave a ρ value of ca.–1.5, indicating that the reaction was promoted by electron-releasing groups para to the oxime function. Increasing the dielectric constant of the solvent raises the reaction rate; we have therefore proposed the formation of an ionic intermediate, after fast attack of carbon ...