Abstract
The formation of stable and potentially hazardous compounds as a result of photochemical transformation of pharmaceutical substances in the aquatic environment implies a demand for standard compounds within environmental analysis. The major phototransformation products of diclofenac are comprised of substituted diphenylamines and carbazoles. Substituted diphenylamines were synthesized by Ullmann condensation reactions between anilines and halobenzenes. Monochlorocarbazoles were obtained from palladium-catalyzed intramolecular coupling reactions of monochlorinated diphenylamines, photocyclization of dichlorinated diphenylamines or by direct chlorination of carbazole. The availability of synthetic photoproducts of diclofenac is of critical importance for further studies on the environmental fate as well as the ecotoxicological effects of the drug in the environment.
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Acknowledgments
The Finnish Graduate School in Environmental Science and Technology (EnSTe) and Walter och Lisi Wahls Stiftelse för Naturvetenskaplig Forskning are gratefully acknowledged for financial support. We also wish to thank Markku Reunanen for HRMS-analyses.
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Svanfelt, J., Kronberg, L. Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac. Environ Chem Lett 9, 141–144 (2011). https://doi.org/10.1007/s10311-009-0259-1
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DOI: https://doi.org/10.1007/s10311-009-0259-1