Oxidation of dicyclopentadiene in surface water

Electron impact (EI) and chemical ionization gas chromatography/mass spectrometry were used to identify four oxygenated derivatives and characterize a fifth derivative of dicyclopentadiene in methylene chloride extracts of wastewater and ground water from the Rocky Mountain Arsenal near Denver, Colorado. Based on their EI fragmentation patterns and resistance to trimethylsilylation, putative structures of these derivatives were proposed, and authentic standards were synthesized. For structural confirmation, aliquots of each water extract were spiked with a synthetic standard, and coelution of each of four environmental dicyclopentadiene derivatives with one of the standards was demonstrated on three different capillary gas chromatography columns. In addition, the EI mass spectra of each of the four environmental derivatives and the corresponding synthetic standards were found to be essentially identical. Two monoepoxides, one ketone and a monoepoxide‐ketone derivative of dicyclopentadiene were identified in wastewater from a sewage treatment facility that had been contaminated by ground water. An extract of activated charcoal that had been used to remove dicyclopentadiene wastes from contaminated ground water was found to contain the same ketone derivative, dicyclopentadien‐1‐one, but no epoxide derivatives. Next, it was demonstrated in vitro that the three monooxygenated dicyclopentadiene derivatives could be formed by light‐catalyzed autoxidation independently of microbial metabolism.