Initial rate studies of the oxygenation (50-70 degrees C) of 2,5-dimethylpyrrole (DMP), in nitrobenzene, reveal that this reaction is second order overall and first order in both DMP and O-2. The presence of an equimolar concentration (based on DMP) of the phenolic antioxidant BHT does not inhibit the initial rate of DMP oxygenation. With dodecane or toluene, as solvent, DMP oxygenation (70-120 degrees C) is approximately first order in both DMP and O-2. DIMP oxygenation in dodecane in the presence of 1 or 3 equiv of BHT results in an approximate 52% reduction in the rate of DMP oxygenation. In addition, the oxygenation of 1-deuterated (ND) DMP (in deuterated methanol) does not exhibit a primary kinetic isotope effect. In light of these experimental observations, both the mechanism of DMP oxygenation and its potential relevance with respect to the oxidative degradation of petroleum products are discussed. Finally, experimental evidence from simulated oxidative degradation (LPR 100 degrees C) of a JP-5 jet fuel and a JP-5 jet fuel blending stock are presented to illustrate the relevancy of the DMP model compound study to actual fuel oxidative degradation.