201872-27-7Relevant academic research and scientific papers
An unusual carbon-carbon bond scission reaction with molecular oxygen under mild conditions; formation of piperidines from 1-azabicyclo[2.2.2]octanes
Norris, Timothy,Santafianos, Dinos,Bordner, Jon
, p. 3679 - 3684 (1997)
Molecular oxygen reacts with 2-(1-phenylethyl)- and 2-benzhydryl-3-alkylimino-1-azabicyclo[2.2.2]-octanes 1-7 in neutral solution at room temperature to form 1-acylpiperidine-4-carboxylic acid N-alkylamides 8-14. During the transformation two new carbonyl bonds are formed and a carbon-carbon bond is cleaved. The transformation is quite general provided the 2-substituent of the imine is of sufficient steric bulk, such as the 2-(1-phenylethyl) or 2-benzhydryl groups. No reaction is observed in the absence of a 2-substituent, as in the case of imine 15.
