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Influence of solvents on the reaction of 5-nitro-2-furylvinyl-trimethylammonium bromide with piperidine

V.V. Kravchenko, A.F. Popov, L.I. Kostenko, A.A. Kotenko, D. Végh, and J. Kováč

Institute of Physical Organic and Coal Chemistry, Academy of Sciences, SU-340 114 Donetsk


Abstract: The kinetics of reactions of (E)-[β)-(5-nitro-2-furyl)vinyl]trimethylammonium bromide, (E)-2-(β-bromovinyl)-5-nitrofuran, and 2-ethynyl-5-nitrofuran with piperidine in various solvents at 25 °C has been studied. The comparison of the obtained data has shown that despite the strongly electron-accepting nature of the ammonium group furylvinylammonium salts actually do not excel the corresponding vinyl halides and ethynylfurans in their reactivity. The reason for this lies in different manifestations of solva- tion effects of the medium in above reactions proceeding differently by their transition states nature. The influence of nonspecific and specific solvation of solvents on the rate of interaction between a furylvinyltrimethylammonium salt and piperidine has been investigated.

Full paper in Portable Document Format: 415a593.pdf


Chemical Papers 41 (5) 593–600 (1987)

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