1281963-93-6Relevant academic research and scientific papers
Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism
Stankovic, Sonja,Catak, Saron,D'Hooghe, Matthias,Goossens, Hannelore,Abbaspour Tehrani, Kourosch,Bogaert, Piet,Waroquier, Michel,Van Speybroeck, Veronique,De Kimpe, Norbert
, p. 2157 - 2167 (2011)
The synthetic utility of N-alkylidene-(2,3-dibromo-2-methylpropyl)amines and N-(2,3-dibromo-2-methylpropylidene)benzylamines was demonstrated by the unexpected synthesis of 3-methoxy-3-methylazetidines upon treatment with sodium borohydride in methanol under reflux through a rare aziridine to azetidine rearrangement. These findings stand in contrast to the known reactivity of the closely related N-alkylidene-(2,3-dibromopropyl)amines, which are easily converted into 2-(bromomethyl)aziridines under the same reaction conditions. A thorough insight into the reaction mechanism was provided by both experimental study and theoretical rationalization.
