Trifluoroacetonitrile Oxide

Article abstract of DOI:10.1021/jo00179a031

Trifluoroacetonitrile oxide (1) is a reactive intermediate that can be generated by the dehydrochlorination of trifluoroacetohydroximoyl chloride (2) with base.It reacts with mercaptans and amines in a stereospecific manner to give Z oximes 3 and 15 and forms a cycloadduct (10) with benzonitrile.In the absence of trapping agents, it dimerizes to give either the expected furoxan dimer 7 or the unusual dioxadiazine dimer 8, depending upon conditions.A convenient synthesis for 2 based on hydroxylamine hydrochloride, trifluoroacetic anhydride, and PCl3 was developedto make 1 easily accessible.