This article is cited in 5 papers

Communications

The first example of fluoro-Meinwald rearrangement

S. A. Ponomarev^a, R. V. Larkovich^a, A. S. Aldoshin^a, V. N. Khrustalev^bc, V. G. Nenajdenko<sup>a

a</sup> Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^c Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation

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.

Keywords: nitrostyrene, Diels–Alder reaction, norbornene, norbornadiene, epoxidation, Meinwald rearrangement, acyl fluorides, bicyclo[3.1.0]hex-2-ene-6-carboxylic acids, organofluorine compounds.

Language: English

DOI: 10.1016/j.mencom.2023.02.012

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