Solvent-controlled selective transformation of 2-bromomethyl-2- methylaziridines to functionalized aziridines and azetidines

Stanković, Sonja; Goossens, Hannelore; ÇATAK, ŞARON; Tezcan, Meniz; Waroquier, Michel; Van Speybroeck, Veronique; D'Hooghe, Matthias; De Kimpe, Norbert

doi:10.1021/jo202637a

Solvent-controlled selective transformation of 2-bromomethyl-2- methylaziridines to functionalized aziridines and azetidines

Stanković S., Goossens H., ÇATAK Ş., Tezcan M., Waroquier M., Van Speybroeck V., ...Daha Fazla

Journal of Organic Chemistry, cilt.77, sa.7, ss.3181-3190, 2012 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 77 Sayı: 7
Basım Tarihi: 2012
Doi Numarası: 10.1021/jo202637a
Dergi Adı: Journal of Organic Chemistry
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.3181-3190
Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
Boğaziçi Üniversitesi Adresli: Evet

Özet

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. © 2012 American Chemical Society.