1281963-86-7Relevant academic research and scientific papers
Solvent-controlled selective transformation of 2-bromomethyl-2- methylaziridines to functionalized aziridines and azetidines
Stankovic, Sonja,Goossens, Hannelore,Catak, Saron,Tezcan, Meniz,Waroquier, Michel,Van Speybroeck, Veronique,D'Hooghe, Matthias,De Kimpe, Norbert
experimental part, p. 3181 - 3190 (2012/05/20)
The reactivity of 2-bromomethyl-2-methylaziridines toward oxygen, sulfur, and carbon nucleophiles in different solvent systems was investigated. Remarkably, the choice of the solvent has a profound influence on the reaction outcome, enabling the selective formation of either functionalized aziridines in dimethylformamide (through direct bromide displacement) or azetidines in acetonitrile (through rearrangement via a bicyclic aziridinium intermediate). In addition, the experimentally observed solvent-dependent behavior of 2-bromomethyl-2-methylaziridines was further supported by means of DFT calculations.
Synthesis of 3-functionalized 3-methylazetidines
Stankovi?, Sonja,D'Hooghe, Matthias,Abbaspour Tehrani, Kourosch,De Kimpe, Norbert
scheme or table, p. 107 - 110 (2012/01/17)
1-t-Butyl- and 1-(4-methylbenzyl)-3-bromo-3-methylazetidines were prepared from the corresponding N-(2,3-dibromo-2-methylpropylidene)alkylamines and their propensity to undergo nucleophilic substitution at the 3-position by different nucleophiles was asse
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 (2011/05/14)
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.
