The Journal of Organic Chemistry

Cyclic imides. 14. Kinetics of the reaction of 3-fluoro-N-methylphthalimide with secondary amines. An example of imide-activated aromatic nucleophilic substitution

LR Caswell, ME Goldsmith

Index: Caswell, Lyman R.; Goldsmith, Miriam E. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5101 - 5104

Full Text: HTML

Citation Number: 7

Abstract

The kinetics of the reactions of 3-fluoro-N-methylphthalimide with pyrrolidine, piperidine, and morpholine in acetonitrile and in benzene have been measured under pseudo-first-order conditions at 25" C on the basis of the rate of increase of absorbance of the aminophthalimide end product. The reactions display kinetic behavior typical of the SNAr bimolecular addition-elimination mechanism of aromatic nucleophilic substitution. Base ...