Action of atomic fluorine on E- and Z-2-butene

Article abstract of DOI:10.1016/S0022-1139(00)80217-1

Irradiation of N₂F₄(NF₂) with E- and Z-2 butene in the gas phase leads to addition of F and NF₂ across the double bond in a non-stexeoselective manner and abstraction of H to give 2- butenyl radicals which interconvert rapidly before being trapped by NF₂ to yield E- and Z-1- difluoroamino-2-butene and 3-difluoramino-1-butene. The configurational instability of the 2- butenyl radicals is attributed to the exothermicity of F atom abstraction. These results are contrasted with those of other workers who observed that in condensed phase reactions abstraction by t-butoxy radical leads to 2-butenyl radicals which are configurationally stable.