Abstract
The gas-phase co-pyrolysis of styrene with CHClF2 in a flow reactor at 550–650 °C gives 2,3-difluoronaphthalene in two parallel reaction channels. The main channel includes decomposition of CHClF2 to difluorocarbene, whose subsequent cycloaddition to styrene affords 1,1-difluoro-2-phenylcyclopropane. This compound rearranges to 2-fluoroindene giving finally difluoronaphthalene upon the second difluorocarbene cycloaddition and subsequent aromatization of the resulting cycloadduct. The second reaction channel consists in aromatization of 1,1,2,2-tetrafluoro-3-phenylcyclobutane, which is formed by the [2+2]-cycloaddition of styrene to tetrafluoroethylene, a product of difluorocarbene dimerization.
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