[CH:1](=[C:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]=[CH2:18])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].[FH:19].C(=O)([O-])O.[Na+]>ClCCl.N1C=CC=CC=1>[CH2:1]([C:5]1([F:19])[CH2:6][CH2:7][CH:8]([CH:11]2[CH2:12][CH2:13][CH:14]([CH:17]=[CH2:18])[CH2:15][CH2:16]2)[CH2:9][CH2:10]1)[CH2:2][CH:3]=[CH2:4]20.6 g of 4'-but-3-enylidene-4-vinylbicyclohexyl in 40 ml of dichloromethane were cooled to -25° C. 7.523 ml of a 70% solution of hydrogen fluoride in pyridine were then added dropwise with stirring, and the mixture was stirred at -25° C. for 30 minutes and then at RT for a further 8 hours. The reaction solution was poured into a suspension of 40 g of sodium hydrogencarbonate and 800 g of ice-water. The mixture was extracted with three times 150 ml of hexane. The combined organic extracts were washed once with 50 ml of sodium chloride solution, dried using sodium sulphate, filtered and evaporated to a residue. Crystallization from pentane at -25° C. gave 4-but-3-enyl-4-fluoro-4'-vinylbicyclohexyl (C 13 SmB 37 N 80 I, Δn=0.049, Δε=-1.8, viscosity=13 mm2).
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