α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones

α-Fluoroacrylonitriles 2 were synthesized in moderate to good yields by Horner–Wittig (HW) reaction of aldehydes and ketones with (diphenylphosphinoyl)fluoroacetonitrile (1), prepared in situ from commercially available fluoroacetonitrile and diphenylphosphinyl chloride. New synthetic applications of 2 are presented with the one-pot conversion into 2-fluoroallylamines 6 and C-(1-fluorovinyl)nitrones 8 through a diisobutylaluminum hydride (DIBALH)-reduction transimination protocol. The scope and limitations of this procedure are discussed.