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Issue 0, 1966
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Nucleophilic attacks on carbon–carbon double bonds. Part X. Nucleophile-catalysed cis–trans isomerisation of cis-4-nitrochalcone and of diethyl maleate in 95% ethanol

Abstract

The catalytic cis–trans isomerisation of 4-nitrochalcone and of diethyl maleate in the presence of various nucleophiles has been studied spectrophotometrically in 95% ethanol. The reactivity order was: OH > piperidine > N3 > BunNH2 > C6H11·NH2, benzylamine > Prn2NH > Pr12 NH ⋙ Bun3N, C5H5N, Br. The isomerisation is of overall second order (first order in each the substrate and the nucleophil) at low nucleophile concentrations, but the second-order rate coefficients fall with increase in the catalyst concentration. The kinetic behaviour, mechanism and factors influencing the reaction are discussed.

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J. Chem. Soc. B, 1966, 1133-1137
Article type
Paper

Nucleophilic attacks on carbon–carbon double bonds. Part X. Nucleophile-catalysed cis–trans isomerisation of cis-4-nitrochalcone and of diethyl maleate in 95% ethanol

Z. Grünbaum, S. Patai and Z. Rappoport, J. Chem. Soc. B, 1966, 1133 DOI: 10.1039/J29660001133

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