N-flouroamines and their analogues as fluorinating agents in organic synthesis

Published data on the synthesis and use in organic synthesis of compounds c ontaining N-F bonds are surveyed and summarised. The reagents are classifie d into two categories: neutral ones (perfluoro-N-fluoropiperidine, N-fluoro -2-pyridone, N-fluorosulphonamides, N-fluoroalkylamides, N-flourobis(triflo uromethyl)sulphonimide, benzo-1,3,2-dithiazole 1,1,3,3-tetroxide, N-flourop yridinium, and N-fluoroquinuclidinium salts and 1-alkyl-4-fluoro-1,4-diazon iabicyclo[2.2.2]octane). Comparative analysis of the fluorinating ability o f the reagents depending on their structure and the nature of the solvent h as been carried out, taking into account the data of calculations. The poss ibility of fluorinating various classes of organic compounds is discussed. The mechanisms of fluorination by compounds containing N-F bonds are consid ered using kinetic data. The advantages and disadvantages of N-fluoroamines in comparison with elemental fluorine, xenon difluoride and other fluorina tion reagents are considered. The influence of the nature of solvent on the fluorinating ability of N-fluoroamines and their analogues is discussed.