Iodine → 1,1,1,2,2,3,5,5,5-Nonafluoro-4-(trifluoromethyl)pentane

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Perfluoro-2-methylpent-2-ene (3 g) and iodine (1.25 g) were sealed in a 10 mL pressure tube. The tube was cooled to -78° C., evacuated, and charged with 1500 psi of hydrogen at room temperature. The tube was then heated at 240° C. for 1 h, and 260° C. for 15 h. The tube was cooled, vented, and opened The liquid was washed with water, giving 1,1,1,2,2,3,5,5,5-nonafluoro-4-trifluoromethylpentane (1.38 g) which was 99.5% pure by GC analysis GC/IR 3000 cm-1, w (C-H); 1288 cm-1 , vs (C-F); 1228 cm-1, vs (C-F); 691 cm-1, m. 19FNMR (CCl3F as internal standard): -62 ppm, c, 3F; -67 5 ppm, c, 3F; -83.9 ppm, t, 3F; -122-133 ppm, AB, 2F; -212.2 ppm, c, 1F. 1HNMR (CHCl3 as internal standard): 5.27 ppm, dd, 1H; 3.55 ppm, c, 1H. The boiling point of this product was 67° C.

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