Abstract:
Novel fluorinated norbornadienes were synthesized in up to 95% yield by the base-induced elimination of HNO2 from 5-fluoro-5-nitro-6-arylbicyclo[2.2.1]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-bicyclo[3.1.0]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.
Citation:
S. A. Ponomarev, R. V. Larkovich, A. S. Aldoshin, V. N. Khrustalev, V. G. Nenajdenko, “The first example of fluoro-Meinwald rearrangement”, Mendeleev Commun., 33:2 (2023), 188–190
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https://www.mathnet.ru/eng/mendc345
https://www.mathnet.ru/eng/mendc/v33/i2/p188
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