Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride.
نویسندگان
چکیده
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.
منابع مشابه
Intramolecular pi-pi stacking interactions in 2-substituted N,N-dibenzylaziridinium ions and their regioselectivity in nucleophilic ring-opening reactions.
The ring opening of 2-substituted N,N-dibenzylaziridinium ions by bromide is known to occur exclusively at the substituted aziridine carbon atom via an S(N)2 mechanism, whereas the opposite regioselectivity has been observed as the main pathway for ring opening by fluoride. Similarly, the hydride-induced ring opening of 2-substituted N,N-dibenzylaziridinium ions has been shown to take place sol...
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ورودعنوان ژورنال:
- Chemical communications
دوره 18 شماره
صفحات -
تاریخ انتشار 2009