57988-64-4

Upstream product

• 110-91-8 morpholine 
• 150163-13-6 cis/trans 3-bromo-2-methylacrylonitrile 
• 151-50-8 potassium cyanide 
• 158662-96-5 trans-3-benzotriazol-1-yl-1-(N-morpholino)prop-1-ene 
• 158662-82-9 1,3-bis(benzotriazol-1-yl)-1-(morpholin-4-yl)propane 

Relevant 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

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.