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Yun, Sae Young,Catak, Saron,Lee, Won Koo,D’hooghe, Matthias,De Kimpe, Norbert,Van Speybroeck, Veronique,Waroquier, Michel,Kim, Yongeun,Ha, Hyun-Joon Royal Society of Chemistry 2009 Chemical communications Vol.2009 No.18
<P>The ring opening of 2-substituted <I>N</I>,<I>N</I>-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.</P> <P>Graphic Abstract</P><P>The ring opening of 2-substituted <I>N</I>,<I>N</I>-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. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=b822763b'> </P>
Ji, Mi-Kyung,Hertsen, Dietmar,Yoon, Doo-Ha,Eum, Heesung,Goossens, Hannelore,Waroquier, Michel,Van Speybroeck, Veronique,D'hooghe, Matthias,De Kimpe, Norbert,Ha, Hyun-Joon Wiley (John WileySons) 2014 Chemistry - An Asian Journal Vol.9 No.4
<P>1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate was generated as a stable bicyclic aziridinium salt from the corresponding 2-(3-hydroxypropyl)aziridine upon reaction with p-toluenesulfonyl anhydride. This bicyclic aziridinium ion was then treated with various nucleophiles including halides, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening, mediated by the characteristics of the applied nucleophile. On the basis of DFT calculations, ring-opening reactions under thermodynamic control yield piperidines, whereas reactions under kinetic control can yield both piperidines and pyrrolidines depending on the activation energies for both pathways.</P>