Facile Synthesis of Methylenecyclobutyl-Related Compounds via Rearrangement­ of Methylenecyclopropylcarbinols in the Presence of Multifluorosulfonyl­ Fluorides and Base

Abstract

Methylenecyclopropylcarbinols treated with multifluorosulfonyl fluorides and triethylamine form the 3-methylenecyclobutyl fluorides and 3-methylenecyclobutyl (2-methylenecyclo­-propyl)methyl ethers in good to high total yields. A proposed mechanism is based on the obtained results.

Key words

methylenecyclopropylcarbinols - multifluorosulfonyl fluorides - base - rearrangement - etherification

References

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9

The crystal data for 5c has been deposited as CCDC 623472. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Empirical formula: C₁₁H₁₀BrF; formula weight: 241.10; crystal color, habit: colorless, prismatic; crystal system: monoclinic; lattice type: primitive; lattice parameters: a = 4.539 (3) Å, b = 9.933 (6) Å, c = 11.135 (7) Å, α = 90°, β = 93.865 (10)°, γ = 90°, V = 500.9 (5) ų; space group: P2 (1); Z = 2; D_calcd = 1.599 g/cm³; F₀₀₀ = 240; diffractometer: Rigaku AFC7R; residuals: R, Rw: 0.0577, 0.1406.