Synthetic Organic Chemistry with 2-Ethoxy-2-(phenylselenenyl)perfluoroalk-2-enenitrile:  Application to α-Cyanoperfluoroacylation of Aldehydes

(Z)- and (E)-2-Ethoxyperfluoro-2-(phenylselenenyl)alk-2-enenitriles 2−4 prepared by our original method underwent transmetalation on treatment with n-BuLi or EtMgBr, and the successive reaction with aldehyde and ketones afforded the corresponding allylic alcohols 10a−f, 9a, and 11a,b in good to high yields. Hydrolysis of the alcohols gave α-cyano-α,β-unsaturated perfluoroalkyl ketones 13a−c, 13e, 12a, and 15a. α-Cyanoperfluoroalkyl ketones were easily converted to α,β-unsaturated 3-aryl-2-cyanoallylic alcohols 18−22 having interesting biological activities and chemical reactivities.