Reaction of perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene withaniline and its derivatives

Reaction of perfluoro-2-methylpent-2-ene (1) and perfluoro-5-azanon-4-ene ( 2) with aniline, 4-fluoroaniline, 4-methoxyaniline and 2,6-dimethylaniline in the presence of Et3N provides derivatives of quinoline and quinozaline, whereas reaction of 2 yields diazetine derivatives with 2- and 4-nitroanili nes, 2,6-dichloroaniline and pentafluoroaniline. The structure of [2-(1,1,2 ,2,3,3,3-pentafluoroethyl)-3-triomethyl-quinoline-4-yl]-phenylamine is conf irmed by X-ray structural data. The routes of reactions and the F-19 and C- 13 NMR spectral data of the products are discussed. (C) 2000 Elsevier Scien ce S.A. All rights reserved.