Mécanisme de la réaction de cyclisation en milieu aqueux de carbanilates de propargyle en méthylène-4 oxazolidinones-2 |
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| Authors: | Yolande MespliÉ Michel Bergon Jean-Pierre Calmon |
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| Institution: | Laboratoire de Chimie Organique Biologique, Ecole Nationale Supérieure Agronomique, Institut National Polytechnique de Toulouse, 145 avenue de Muret, 31076 Toulouse Cédex, France |
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| Abstract: | The alkaline hydrolysis of propargyl 3-chlorocarbanilates was investigated kinetically using uv spectropotometry. The cyclization to 4-methoylene-2-oxazolisinones proceeds via the numcleophilic attack of the substrate anion concomitantly with that of the hydroxide ion on the triple bond. The nucleophilic attack leads directly to the heterocycle whereas the hydroxide ion attack gives rise to a ketocarbamate which is then cyclized to the oxazolidione. |
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