Kinetics of N-bromination of 2-oxazolidinone

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 < NBS < HOBr. © 2004 Wiley Periodicals, Inc. Int J Chem Kinet 36: 642–649, 2004