1281963-91-4Relevant 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
scheme or table, p. 2157 - 2167 (2011/05/14)
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.
