The trifluoromethanesulfonyl(" trifyl") group appears to be the most powerful electron- withdrawing group known and we have been examining this effect in a series of synthetic app1ications. I Triflation of nitrogen greatly enhances the potential of that atom to act as a stabilized anion leaving group, CF3S02N-(cf., CF3S02NH2, pKa= 5.8). Accordingly, we examined the behavior of N-triflated amides as acylating agents. These acylating agents ...
[White, Emil H.; DePinto, Jeffrey T.; Polito, Albert J.; Bauer, Ines; Roswell, David F. Journal of the American Chemical Society, 1988 , vol. 110, p. 3708 - 3709]
