The mechanism of vinyl interchange by nuclear magnetic resonance spectroscopy

Tipo de material: Texto

TextoSeries ; Tetrahedron, 22(9), p.3163-3171, 1966Trabajos contenidos:

SLINCKX, G
SMETS, G

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Resumen: mechanism of the vinyl interchange reaction between benzoic acid and vinyl acetate and catalysed by mercury-II acetate and an acetic solution of the BF,-AcOH complex has been investigated by NMR spectroscopy. For this p"pose a/Q?'-trideutero-vinyl acetate and deutero-Oacetic acid have been synthesized. During the course of the vinyl interchange, the vinyl group is transferred as a whole entity from one carboxylate radical to the other without any carbon-hydrogen bond scission. /?-Acetoxy mercuri ethane aa'-diesters postulated aa intermediates of the reaction have been prepared and characterized; these compounds are effectively reaction intermediates. The isolation and structural elucidation of some deuterated ethylidene diestm demonstrates the mechanism of side reactions of the addition of acid to vinyl esters.

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mechanism of the vinyl interchange reaction between benzoic acid and vinyl acetate and catalysed by mercury-II acetate and an acetic solution of the BF,-AcOH complex has been investigated by NMR spectroscopy. For this p"pose a/Q?'-trideutero-vinyl acetate and deutero-Oacetic acid have been synthesized. During the course of the vinyl interchange, the vinyl group is transferred as a whole entity from one carboxylate radical to the other without any carbon-hydrogen bond scission. /?-Acetoxy mercuri ethane aa'-diesters postulated aa intermediates of the reaction have been prepared and characterized; these compounds are effectively reaction intermediates. The isolation and structural elucidation of some deuterated ethylidene diestm demonstrates the mechanism of side reactions of the addition of acid to vinyl esters.

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