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THE PHOTOLYSIS OF 5‐NITROFURFURAL IN AQUEOUS SOLUTIONS: NUCLEOPHILIC SUBSTITUTION OF THE NITRO‐GROUP
Author(s) -
Busker Ruud W.,
Henegouwen Gerard M. J. Beijersbergen
Publication year - 1987
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1987.tb05383.x
Subject(s) - photodissociation , chemistry , nitrite , nitro , aqueous solution , nitrofuran , metabolite , nucleophile , nucleophilic substitution , medicinal chemistry , photochemistry , organic chemistry , catalysis , nitrate , alkyl , biochemistry , biology , genetics
— The photolysis in aqueous neutral solutions of 5‐nitrofurfural (NFA), an important metabolite of nitrofurans used as medicines, was investigated. Upon UV‐A irradiation NFA loses up to 70 mol % nitrite, with formation of 5‐hydroxymethylene‐2(5H)‐furanone, a new substance. When Cl −1 is present 5‐chlorofurfural is an important photoproduct. Photo‐induced addition of either OH or CI −1 , followed by thermochemical elimination of NO 2 −1 , is the proposed mechanism. Furthermore, NFA reacts with nitrite yielding nifuroxim. The possible role of the NFA photolysis in the occurrence of (photo)biological effects of NFA is discussed.