The chlorination reactions of 2-oxazolidinone with hypochlorous acid (HOCl), tert-butyl hypochlorite ( t BuOCl) and N-chlorosuccinimide (NCS) were studied at 25°C, constant ionic strength, and under isolation conditions. The kinetic results obtained in the formation processes of the N-chloro-2-oxazolidinone are summarized in this paper. The kinetics studied showed a first order with respect to the concentration of the each reactant and a complex dependence of the pH on the rate constant. The reactivity order with respect to the chlorinating agent found is k(HOCl) > k( t BuOCl) > k(NCS).

The kinetics of N-bromination of 2-oxazolidinone by transfer of Br from sodium hypobromite, N-bromosuccinimide (NBS), or N-bromoacetamide (NBA) were determined spectrophotometrically, at pH between 4.6 and 12.45 (depending on the brominating agent). The reaction with hypobromite was of first order with respect to both the hypobromite and the substrate. The bromination of oxazolidinone with NBS (or NBA) has been found to be a reversible process of order one with respect to both NBA (or NBA) and oxazolidinone in the forward direction, and order one with respect to SI (or ACAM) and the resulting N-bromo-oxazolidinone in the other. The pH dependence of the reaction rate was in keeping with a mechanism in which all the brominating agents (HOBr, BrO − , NBS and NBA) react predominantly with the anion of the substrate. Bimolecular bromination rate constants increased in the order BrO − < NBA <

aThe kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25°C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pK a units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound.Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline).