Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents |
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Authors: | G I Borodkin P A Zaikin M M Shakirov V G Shubin |
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Institution: | (1) Vorozhtsov Novosibirsk Institute of organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia;(2) Novosibirsk State University, Novosibirsk, Russia |
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Abstract: | Kinetic isotope effects H/D in electrophilic fluorination of aromatic compounds with NF-reagents were investigated. The small values of k H/k D (0.86–1.00) are in agreement with the polar reaction mechanism where the Wheland complex decomposition is not the limiting stage. The fluorination of 1,3,5-trideuterobenzene was established by 1H and 19F NMR spectroscopy to occur with a 1,2-migration of a hydrogen (deuterium) atom. The analysis of Brown-Stock relationship demonstrated that the activity of NF-reagents exceeded that of many known electrophilic systems including halogenation, but it was essentially less than the activity of elemental fluorine. |
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