Phenyltelluroacrylonitriles and phenylselenoacrylonitriles as precursors of (Z)-α-phenylseleno-α,β-unsaturated aldehydes, β-amino-α-phenylselenonitriles and Diels–Alder adducts

Reaction of cyanomethylphosphonate with aryl selenenyl (or tellurenyl) halides and aldehydes, under basic conditions, provides α-phenylseleno or α-phenyltelluro acrylonitriles in good yields. Reaction of the α-phenylseleno acrylonitriles with dienes furnishes the corresponding adducts while reaction with amines furnishes α-phenylseleno-β-amino nitriles. Selective reduction of the cyano group with DIBAL-H results in the α-phenylseleno-α,β-unsaturated aldehydes.