Convenient Preparations of Imines and Symmetrical Secondary Amines Possessing Primary or Secondary Alkyl Groups

Rotaxane or Pseudorotaxane? That Is the Question!

“…The ammonium ions used in this investigation were prepared as their hexafluorophosphate salts to (1) augment their solubilities in organic solvents and (2) weaken ion pairing, i.e., to destabilize the reactants' ground-state energy compared to that of their complexes, thus making Δ G ° more negative. The requisite secondary diamine precursors of the salts 2 ·PF 6 − 6 ·PF 6 were prepared (Scheme ) by two methods: specifically, by Route Avia a reductive amination sequence, in which the appropriate aldehyde and amine were condensed to produce an imine that was subsequently reduced with NaBH 4 and by Route Bvia the condensation of the appropriate aldehyde with NH 3 and benzotriazole (BtH), followed by reduction of the resultant bis[1-(benzotriazol-1-yl)alkyl]amine with LiAlH 4 . The secondary diamines obtained by these methods were then converted into the salts 2 ·PF 6 − 6 ·PF 6 by heating with hydrochloric acid, followed by counterion exchange from chloride to hexafluorophosphate.…”

Properties and Synthetic Utility ofN-Substituted Benzotriazoles

“…However, benzotriazole does react with ketones in the presence of phosphorus oxychloride to give gem-dibenzotriazol-1-ylalkanes, as exemplified by the preparation of 2,2-dibenzotriazol-1-ylpropane (111) from acetone (Scheme 40). 27 Mannich-type condensation reactions of benzotriazole with an aldehyde and an diaryl oxime under acid catalysis affords the corresponding O-(1-benzotriazolylalkyl)oximes (112) in moderate yields (Scheme 41).…”

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

“…The condensation reaction of benzotriazole, aryl aldehydes, and ammonia results in the formation of N-arylmethylene[(benzotriazol-1-yl)arylmethyl]amines 71 [78] Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles eliminates a benzotriazolide anion spontaneously to give 1,2-pyrroline 74 with a cis-relative configuration (Scheme 25) [79].…”