tert-Butyl hydroperoxide → 2,3-Epoxy-5-(perfluorooctyl)bicyclo[2.2.1]heptane

Participants

Reaction Steps

128 g (250 mmol) of the Diels-Alder reaction product of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decene (perfluorooctylethene) and cyclopentadiene are mixed in 10 ml of dry toluene with 815 mg (2.5 mmol) of molybdenum acetylacetonate, and 104 ml of a 3.6 molar solution of t-butyl hydroperoxide in toluene (375 mmol) is added dropwise at 28° C. within 2 hours. During this period, the temperature rises to 40° C. The solution is then held at 65°C. for 14 hours, and subsequently at 80° C. for another 2 hours. Thereaction mixture is filtered over magnesium silicate, followed by washing with two 20 ml portions of toluene. The low-boiling components are stripped off on a rotary evaporator. The residue obtained is taken up in 50 ml of hexane and left to crystallize for 12 hours at -28° C. Theresulting slurry of solids is filtered off with suction and dried at room temperature in an oil pump vacuum.

Provenance & Evidence