A new synthesis of allenic nitriles from ynones via cyano phosphates

Article abstract of DOI:10.1248/cpb.40.21

Ynone cyanohydrin diethyl phosphates (cyano phosphates) 2 reacted regioselectively with higher-order cuprates 3, generated from 2-thienyl(cyano)copper lithium and n-butyl lithium, to give trisubstituted allenic nitriles 4 through an SN2' process in good yields. On the other hand, reaction of an excess of dialkyl copper lithium with ynone cyano phosphates 2 afforded allylic nitriles 5, via allenic nitriles 4.