Oxygen → Perfluoro(1-bromo-6,7-epoxy-4-oxaheptane)

Participants

Reaction Steps

A 100-ml metal tube containing 20.0 g (0.053 mol) of perfluoro(7-bromo-4-oxa-1-heptene) from Part C and 60 ml of CF2ClCFCl2 was heated at 140° while O2 was injected incrementally over a 4 h period until absorption ceased. The mixture was cooled, gases vented, and the liquid product fractionated to give 6.9 g (33%) of perfluoro(1-bromo-6,7-epoxy-4-oxaheptane), bp 94°-95°. IR (CCl4): 6.50 (epoxide), 8-9μ (CF, C-O) with weak band indicating COF impurity near 5.3μ. NMR (CCl4): 19F -65.6 (t of m, JFF 9.8 Hz, 2F, CF2Br), -80.2 (AB multiplets 2F, CF2O), -80.4 (AB multiplets, 2F, CF2O), -121.9 (m, 2F, CF2), and -156.6 ppm (t of m, JFF 17.6 Hz, 1F, CF), with AB multiplets for ring CF at -10368 and -10409 Hz (d of d of m, JFF 18.5, 9.8 Hz, 1F) and -10596 and -10637 Hz (d, JFF 17.3 Hz, 1F).

Provenance & Evidence