[Cl:1][C:2]([SH:5])([Cl:4])[Cl:3].[F:6][C:7]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:8][OH:9].[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:7]([CH2:8][O:9][S:5][C:2]([Cl:4])([Cl:3])[Cl:1])([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[F:6]Perchloromethylmercaptan (5.6 g, 0.03 mol) and 2-fluoro-2,2-dinitroethanol (5.0 g, 0.033 mol) in 30 ml of methylene chloride was combined with 0.3 g of tetrabutyl ammonium chloride in 20 ml of water and the vigorously stirred mixture was cooled in an ice-salt bath. A solution obtained by diluting 2.6 g of 50 percent aqueous sodium hydroxide with 3 ml of water was added dropwise keeping the temperature at 0° C. Separation of the methylene chloride layer and removal of the solvent gave 8.2 g of an oil which was extracted with 2×40 ml of hexane. The combined extracts were passed through a silica gel 60 pad and the pad was washed with benzene. Removal of solvent gave 5.9 g (65 percent) of an oil which was essentially pure by TLC and GLC analysis; H-NMR (CDCl3): δ 5.37 (d); mass spectrum (C.I.): m/e 304, 302, 267, 269.
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