159789-44-3Relevant academic research and scientific papers
PROPENYLIDENIMINIUM CATIONS AND 3-(BENZOTRIAZOL-1-YL)-1-AMINO-1-PROPENES BY THE ELIMINATION OF BENZOTRIAZOLE FROM 1,3-BIS(BENZOTRIAZOL-1-YL)PROPYLAMINES
Katritzky, A. R.,Rachwal, S.
, p. 1653 - 1671 (2007/10/02)
1,3-bis(Benzotriazol-1-yl)-N,N-disubstituted propylamines eliminate one mole of benzotriazole on treatment with sodium hydride to give 3-(benzotriazol-1-yl)-1-propen-1-ylamines.In these enamines, the previously unreactive second benzotriazolyl moiety can then undergo ionization to form (2-propenylidene)iminium cations, as was demonstrated by crossover experiments.The propenylideniminium cation undergoes nucleophilic attack by a Grignard reagent either at the first carbon atom to produce the corresponding C-1 substituted allylamines or at the third carbon atom to give enamines.The orientation depends strongly on the conditions and the basicity of the starting amine.Reaction of 2-propenylidenemorpholinium cation (15) with cyanide anions gives 3-morpholinomethacrylonitrile.
