title: Solvent-controlled selective transformation of 2-bromomethyl-2-methylaziridines to functionalized aziridines and azetidines.
abstract: 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.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Sonja
authors.initials: S
authors.lastname: Stanković
authors.forename: Hannelore
authors.initials: H
authors.lastname: Goossens
authors.forename: Saron
authors.initials: S
authors.lastname: Catak
authors.forename: Meniz
authors.initials: M
authors.lastname: Tezcan
authors.forename: Michel
authors.initials: M
authors.lastname: Waroquier
authors.forename: Veronique
authors.initials: V
authors.lastname: Van Speybroeck
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
chemical_list: D001384:Azetidines; D001388:Aziridines; D012997:Solvents; D013455:Sulfur; D002244:Carbon; D010100:Oxygen