Reactions of salicylaldehyde with tris(pentaf luorophenyl)silanes and secondary amines

Reactions of tris(pentafluorophenyl)silanes RSi(C₆F₅)₃ with salicylaldehyde and secondary amines were studied. The reactions afforded α-pentafluorophenyl-substituted amines. Silanes RSi(C₆F₅)₃ (R = Me, Ph, C₆F₅, CH₂CH=CH₂, and CH=CH₂) were found to be efficient reagents for transfer of the C₆F₅ group to the iminium cation generated from salicylaldehyde and amine. However, tris(pentafluorophenyl)phenylethynyl-and tris(pentafluorophenyl)silanes were not able to serve as a source of a fluorinated substituent because of competitive transfer of acetylenide fragment or hydride. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 498–503, March, 2006.