Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: Bromide versus hydride

Yun, Sae; ÇATAK, ŞARON; Lee, Won; D'Hooghe, Matthias; De Kimpe, Norbert; Van Speybroeck, Veronique; Waroquier, Michel; Kim, Yongeun; Ha, Hyun-Joon

doi:10.1039/b822763b

Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: Bromide versus hydride

Yun S. Y., ÇATAK Ş., Lee W. K., D'Hooghe M., De Kimpe N., Van Speybroeck V., ...Daha Fazla

Chemical Communications, sa.18, ss.2508-2510, 2009 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Basım Tarihi: 2009
Doi Numarası: 10.1039/b822763b
Dergi Adı: Chemical Communications
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.2508-2510
Boğaziçi Üniversitesi Adresli: Evet

Özet

The ring opening of 2-substituted N,N-dibenzylaziridinium ions by bromide exclusively occurs at the substituted aziridine carbon atom in a stereospecific way, whereas the opposite regioselectivity was observed for hydride-induced ring opening at the unsubstituted position; furthermore, this unprecedented hydride-promoted reactivity was validated by means of Density Functional Theory (DFT) calculations. © The Royal Society of Chemistry 2009.