The structure of isamic acid, prepared by the reaction of isatin with ammonia, has been established. It is that of the ylid XIIa or XIIc, different from the ylid XIIb first suggested by the present authors in an earlier communication. The difference lies in an unsuspected exchange of nitrogen functions.The nature of the oxidation products with hydrogen peroxide (VII), with nitric acid, and with potassium permanganate (XXVII) has been elucidated; these do not differ from those suggested earlier.In the Appendix the action of diazomethane on N-acetyl isatoic acid is described. Three molecules of reagent are consumed in esterification, homologation, and epoxide formation.
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