Nucleophilic Substitution Reactions of Heterocyclic Amines and Acyclic Diamines with Chlorofluoroolefins and Hexafluoropropylene Oxide

Abstract

The reactions of CH3N(H)CH2CH2N(H)CH3, CH3N(H)CH2CH2CH2N(H)CH3, and the cyclic amines piperazine, N-phenylpiperazine, and N-methylpiperazine with both cyclic and acyclic 1,2-dichloroperfluoroolefins are reported. Nucleophilic attack occurs at olefinic carbon, followed, in some cases, by cyclization and β-elimination. A variety of unusual polyfluorinated tertiary amines and heterocycles are synthesized. © 1994, American Chemical Society. All rights reserved.