Tetraaminoethylenes. I. The Preparation and Some Reactions of Tetrapiperidino- and Tetramorpholinoethylene

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Abstract
The preparation of new tetraaminoethylenes was attempted by the reaction of chlorotrifluoroethylene (CTFE) with several amines. It has been found that CTFE reacted with piperidine and morpholine to give tetrapiperidino- (TPE) and tetramorpholinoethylene (TME) in moderate yields respectively, although no tetraaminoethylenes were formed in the reactions with diethylamine, pyrrolidine, aniline, N-alkylaniline, and diphenylamine. Also, it has been made clear that the compounds whose structures were previously assigned to the tetraaminoethylenes, obtained from 1,1-dimethoxytrimethylamine or ethyl orthoformate and secondary amines are the corresponding triaminomethanes. It has been found that TPE and TME reacted with halogens, halogen-, nitrocompounds, and aromatic carboxylic acids to form mainly the corresponding oxamidinium salts.

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