Reaction of alpha, beta-Unsaturated Carbonyl Compounds with Ethyl Phenylacetate Carbanions. A Synthesis of Substituted Cyclohexanones PDF

Keywords

Michael, chemistry, cyclohexanones

Abstract

The Michael acceptors (chalcones II) react with the ethyl phenylacetate carbanion I in the presence of sodium hydride at room temperature and yield the corresponding Michael products: gamma- aroyl butyrates III(from one mole each of I and II), the corresponding acids IV, or 2, 4-diaroyl- cyclohexanones V(from mole I and two moles of II). The nature of these products depends on the reaction conditions. The mechanism of the formation of the cyclohexanone derivatives (Va-g) as well as the regression of the Michael reaction are discussed.. The structure of all products were inferred by chemical and spectroscopic methods.