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An unexpected course of the Meisenheimer reaction : aryl phosphates in the reaction of phosphoryl chloride with 2, 3-diphenylquinoxaline-N1-oxide.

par Nasielski, Jacques ;Heilporn, Sylvie ;Hinkens, Raymonde ;Evrard, France
Référence Tetrahedron, 43, 19, page (4329-4338)
Publication Publié, 1987

Article révisé par les pairs

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Résumé :

Contrary to what is observed with other π-deficient heteroaromatic N-oxides, the reaction of 2, 3-diphenylquinoxaline-N1-oxide with OPCl3 gives only very poor yields of chlorinated quinoxalines. It is shown that the major product arises from an unprecedented attack by the nucleophilic oxygen atom of the reagent at a carbon atom of the homocycle of the O-phosphorylated N-oxide, leading ultimately to the corresponding mono- (or di-) aryl ester of phosphoric acid. Using a much smaller excess of OPCl3 and dilution of the medium with an inert solvent strongly increase the yield of chlorination products. © 1987.