Reaction of chlorofluorocarbene with with cyclopentadiene

Fluorinated Carbenes

“…The high-temperature thermolysis of dichlorofluoromethane in a platinum or quartz flow-type reactor produced chlorofluoromethylene, which dimerized in the absence of a trapping agent . In the presence of cyclopentadiene, fluorobenzene, hydrogen chloride, and 1,2-dichloro-1,2-difluoroethene were the major reaction products (eq 68) . Similarly, the pyrolysis of dichlorofluoromethane in the presence of indene produced 2-fluoronaphthalene in 55% yield …”

“…331 In the presence of cyclopentadiene, fluorobenzene, hydrogen chloride, and 1,2-dichloro-1,2-difluoroethene were the major reaction products (eq 68). 332 Similarly, the pyrolysis of dichlorofluoromethane in the presence of indene produced 2-fluoronaphthalene in 55% yield. 333 Remlinger reported that chlorofluorocarbene, produced by the dehydrohalogenation of dichlorofluoromethane, reacted with diazo compounds, such as diphenyldiazomethane (101) and diazofluorene, to generate olefins in respective yields of 63 and 67% (eq 69).…”