Poly(N-vinylpyrrolidone) crosslinked with tetraethyleneglycol diacrylate was prepared and used as solid support for immobilizing bromine function. The resin bound hydrotribromide was found to be an efficient reagent for the oxidation of alcohols and dibromination of alkenes. The role of the macromolecular matrix in dictating the efficiency of the oxidizing reagent was elucidated by preparing crosslinked polyvinylpyrrolidone resins with varying mole percent of cross-linking agent. Studies revealed that the extent of functionalisation as well as the reactivity of the oxidizing function was highly dependent on the degree of crosslinking of the macromolecular matrix. The effect of various reaction conditions such as the temperature, solvent and molar concentration of the reagent was also examined in order to find the optimum conditions for oxidising reactions. (C) 2005 Elsevier B.V. All rights reserved.