Difluorocarbene

[1] Although highly reactive, difluorocarbene is an intermediate in the production of tetrafluoroethylene, which is produced on an industrial scale as the precursor to Teflon (PTFE).

The non-bonding electrons of the carbene now need to be placed either double in the rather low energy sp2 orbital on carbon or in the highest anti-bonding level of the MO-system.

[2] [4] Thermal decomposition of sodium chlorodifluoroacetate in the presence of triphenylphosphine and an aldehyde allows for a Wittig-like reactions[5] In this case, (C6H5)3P=CF2 is proposed as an intermediate.

Alternatively, dehydrohalogenation of chlorodifluoromethane or bromodifluoromethane using alkoxides or alkyllithium also produces difluorocarbene: A variant of this reaction is using ethylene oxide in conjunction with a catalytic amount of quaternary ammonium halide at elevated temperature.

This is an attractive method for the synthesis of difluorocyclopropanes as hexafluoropropylenoxide is inexpensive and the byproduct trifluoroacetyl fluoride is a gas.