Compound 1

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InChIKey PQJGSPVYVGXTJW-JMVOWJSSSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

8 (14.0 mg, 0.04 mmol) was dissolved in triethylaminetrihydrofluoride (1 mL) and heated by microwave irradiation (50 W, 120 ˚C) for 2 × 2 h. The resulting sticky brown material was reconstituted with ethyl acetate (10 mL) and poured into saturated aqueous sodium hydrogen carbonate solution (20 mL). The layers were separated, and the aqueous phase was re-extracted with ethyl acetate (3 × 10 mL). The combined organic phase was washed with brine (10 mL), dried over MgSO₄, filtered and concentrated in vacuo, affording a brown gum. Purification of the gum by repeated silica gel chromatography, eluting with dichloromethane and methanol (98:2), furnished cis-1,2,3,4,5,6-hexafluorocyclohexane 1 (ca. 0.8 mg, 10%) as a gum: ¹H NMR (500 MHz, CD₂Cl₂): δ 5.45–5.25 (m, 3H, H_eq overlaps with CD₂Cl₂ signal, confirmed by 2D ¹H–¹⁹F HMBC), 4.71­–4.11 (m, 3H, H_ax); ¹⁹F NMR (470 MHz, CD₂Cl₂): δ -212.8 (app d, 3F, J = 37.6 Hz, F_eq), -217.1 – -217.6 (m, 3F, F_ax); ¹⁹F{¹H} NMR (470 MHz, CD₂Cl₂): δ -212.8 (3F, br s, F_eq), -217.3 (br s, 3F, F_ax); HRMS-APCI (m/z): [M+NH₄]⁺ calcd. for C₆H₁₀F₆N, 210.0712; found, 210.0713.