The first example of fluoro-Meinwald rearrangement |
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| Institution: | 1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. Peoples Friendship University of Russia (RUDN University), 117198 Moscow, Russian Federation;3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. National Research University Higher School of Economics (HSE University), 101000 Moscow, Russian Federation;3. G. V. Plekhanov Russian University of Economics, 117997 Moscow, Russian Federation;1. North-Caucasian Zonal Research Veterinary Institute, 346406 Novocherkassk, Russian Federation;2. Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, Russian Federation;3. North-Caucasus Federal University, 355017 Stavropol, Russian Federation;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;3. V. I. Vernadsky Institute of Geochemistry and Analytical Chemistry, Russian Academy of Sciences, 119334 Moscow, Russian Federation;4. N. I. Pirogov Russian National Research Medical University, 117997 Moscow, Russian Federation;1. A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, 420088 Kazan, Russian Federation;2. Kazan National Research Technological University, 420015 Kazan, Russian Federation;1. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;2. Department of Fundamental Physical and Chemical Engineering, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;3. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;4. Institute of Microelectronics Technology and High Purity Materials, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation |
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| Abstract: | Novel fluorinated norbornadienes were synthesized in up to 95% yield by the base-induced elimination of HNO2 from 5-fluoro-5-nitro-6-arylbicyclo2.2.1]hept-2-enes prepared, in turn, by the Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclopentadiene. The subsequent epoxidation initiated the Meinwald type rearrangement affording 6-aryl-bicyclo3.1.0]hex-2-ene-6-carboxylic acid fluorides as individual (1SR,5RS,6RS)-diastereomers. The transformation is the first example of fluoro-Meinwald rearrangement to form the corresponding acyl fluorides. |
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| Keywords: | nitrostyrene Diels–Alder reaction norbornene norbornadiene epoxidation Meinwald rearrangement acyl fluorides bicyclo[3 1 0]hex-2-ene-6-carboxylic acids organofluorine compounds |
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