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Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride
- Yun, Sae Young;
- Catak, Saron;
- Lee, Won Koo;
- D'hooghe, Matthias;
- De Kimpe, Norbert;
- 외 4명
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40초록
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.
키워드
SUBSTITUTION REACTIONS; AZIRIDINIUM IONS; AMINES; DENSITY; SALTS; 2-(CYANOMETHYL)AZIRIDINES; THERMOCHEMISTRY; REACTIVITY; FLUORIDE
- 제목
- Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride
- 저자
- Yun, Sae Young; Catak, Saron; Lee, Won Koo; D'hooghe, Matthias; De Kimpe, Norbert; Van Speybroeck, Veronique; Waroquier, Michel; Kim, Yongeun; Ha, Hyun-Joon
- DOI
- 10.1039/b822763b
- 발행일
- 2009
- 유형
- Article
- 호
- 18
- 페이지
- 2508 ~ 2510