Tetrahedron Letters

Triflamides: new acylating and triflating reagents

JB Hendrickson, R Bergeron

Index: Hendrickson,J.B.; Bergeron,R. Tetrahedron Letters, 1973 , # 46 p. 4607 - 4610

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Citation Number: 91

Abstract

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 ...

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