Base-promoted elimination of hydrogen fluoride from alkyl fluorides : Reactivity and stereochemistry |
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| Affiliation: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;1. Institute of Structural Macrokinetics and Materials Science, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;2. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. Kazan State Architect and Civil Engineering University, 1 Zelenaya, 420043 Kazan, Russia;2. A.E. Arbuzov Institute of Organic and Physical Chemistry, RAS, 8 Arbuzov Str., 420088 Kazan, Russia;3. Laboratorie de Chimie de Coordination, CNRS, 205 Route de Narbonne, BP 44099, 31077 Toulouse Cedex 4, France |
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| Abstract: | The alcoholate promoted dehydrohalogenation of S-nonyl fluoride and cyclododecyl fluoride, typical straight-chain and, respectively, medium-size cyclic substrates, leads to cis- and trans-alkenes in an approximate ratio of 1 : 3. With bulky bases such as lithium diisopropylamide the trans isomer may be obtained almost exclusively. In general, the elimination of hydrogen fluoride proceeds very slowly. Increase of the base strength has only a moderate effect on the rates. Electrophilic assistance as provided by lithium cations in media of low polarity can, however, considerably accelerate the reaction. - Cyclododecyl fluoride cannot be prepared from cyclododecanol. It is, however, readily accessible by bromofluorination of cyclodecene and subsequent reduction of the adduct with stannane. |
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