Tetrafluoroethylene → HCID 13628172, compound

Participants

Reaction Steps

Methyl perfluoro(5-keto-2-methyl-3-oxahexanoate) (54.4 g, 0.17 mol) was added to a suspension of 17.5 g (0.30 mol) of flame-dried KF in 160 ml of tetraglyme stirred at 10° to 15°. After the mixture had stirred until much of the KF dissolved, 54.9 g (0.34 mol) of iodine monochloride was added with cooling to maintain 20°. The resulting mixture was charged into a dry 400-ml metal tube and shaken while tetrafluoroethylene (36 g, 0.36 mol) was added under pressure. When no further pressure drop occurred, gases were vented. The reaction mixture was poured into ice water and decolorized by the addition of NaHSO3. The aqueous layer was extracted with CF2ClCFCl2, and the combined organic layers were dried over P2O5 and distilled to give 60.0 g (63%) of methyl perfluoro(8-iodo-2,5-dimethyl-3,6-dioxaoctanoate), bp 81° to 83° (16 mm), pure by GC. IR (neat): 2965 (sat'd CH), 1790 (C=O), 1250-1100 cm-1 (CF,C--O). NMR (CCl4): 'H 4.03 ppm (s, OCH3); 19F -64.7 (t,JFF 5.8 Hz, 2F, CF2I), -80.5 (m, 3F, CF3), -83.0 (d, JFF 2.5 Hz, 3F, CF3), -83.7 (m, 2F, CF2O), -132.2 (t of d of m, JFF 16.6, 2.5 Hz, 1F, CF), and -145.9 ppm (t of m, JFF 22 Hz 1F, CF), with AB branches for CF2O at -7375 and -7518 Hz (M,1F) and -8020 and -8162 Hz (d of m, JFF 22 Hz, 1F).

Provenance & Evidence