This article is cited in 4 papers

Communications

Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes

V. E. Shambalova, R. V. Larkovich, S. A. Ponomarev, A. S. Aldoshin, K. A. Lyssenko, V. G. Nenajdenko

Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

Abstract: Novel fluorinated α-epoxycyclohexanes were synthesized in up to 96% yields by epoxidation of the Diels–Alder adducts of β-fluoro-β-nitrostyrenes and 2,3-dimethylbuta-1,3-diene. The epoxidation with m-chloroperoxybenzoic acid and subsequent hydrolysis into diols were found to proceed in a highly stereoselective manner.

Keywords: organofluorine compounds, nitrostyrenes, Diels–Alder reaction, epoxidation, ring-opening, hydrolysis, diols.

Language: English

DOI: 10.1016/j.mencom.2023.06.007

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