Synthetic organic chemistry with 2-ethoxy-2-(phenylselenenyl)perfluoroalk-2-enenitrile: application to alpha-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 alpha-cyano-alpha,beta-unsaturated perfluoroalkyl ketones 13a-c, 13e, 12a, and 15a. alpha-Cyanoperfluoroalkyl ketones were easily converted to alpha,beta-unsaturated 3-aryl-2-cyanoallylic alcohols 18-22 having interesting biological activities and chemical reactivities.
Yoshimatsu
Mitsuhiro
M
Department of Chemistry, Faculty of Education, Gifu University, Yanagido, 1-1, Gifu 501-1193, Japan. yoshimae@cc.gifu-u.ac.jp
Timura
Yoshie
Y
D000215:Acylation; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D009570:Nitriles
D000447:Aldehydes; D007202:Indicators and Reagents; D009570:Nitriles