Kinetics and mechanisms of cyclization in acidic media of N-[(3, 5-dichloroanilino) carbonyl]-N-[(isopropylamino) carbonyl] glycine to hydantoins: iprodione and its …

O Belafdal, M Bergon, M Calmon…

Index: Belafdal, Omar; Bergon, Michel; Calmon, Michelle; Calmon, Jean Pierre Journal of Organic Chemistry, 1989 , vol. 54, # 17 p. 4193 - 4198

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Citation Number: 8

Abstract

N-[(3, 5-Dichloroanilino) carbonyl]-N-[(isopropylamino) carbonyl] glycine (1) cyclizes quantitatively and irreversibly at 50" C in the pH range 0.5-6 by two parallel paths to give iprodione (2) and its isomer 3. Formation of the antifungal agent 2 is characterized by a general base catalysis with carboxylate anions, water, and hydroxide ion (fl= 0.38) and a solvent isotope effect of 2.90. These results are consistent with a specific base catalyzed ...