Tetrahedron

Synthèse et réactivité cathodique des nitriles α insaturés—IV: Alkyl (aryl) oxy-2 phényl-3 propène nitriles

M Cariou, G Mabon, G Le Guillanton, J Simonet

Index: Cariou, M.; Mabon, G.; Guillanton, G. Le; Simonet, J. Tetrahedron, 1983 , vol. 39, # 9 p. 1551 - 1558

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Citation Number: 8

Abstract

A one-pot synthesis of 2-alkyl (aryl) oxy-3-phenyl-propenonitriles, including silica gel Chromatographic separation E and Z-isomers, is described. The attribution of the configurations is carried out by application of Tobey's rule from the chemical shifts of the vinylic protons. These activated olefins do not undergo cathodic coupling, but electrochemical carbon-oxygen bond cleavage. The relative stability of E and Z forms is ...