Issue 5, 2018

Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions

Abstract

Transient bicyclic aziridinium ions are known to undergo ring-expansion reactions, paving the way to functionalized nitrogen-containing heterocycles. In this study, the regioselectivity observed in the ring-expansion reactions of 1-azoniabicyclo[n.1.0]alkanes was investigated from a computational viewpoint to study the ring-expansion pathways of two bicyclic systems with different ring sizes. Moreover, several nucleophiles leading to different experimental results were investigated. The effect of solvation was taken into account using both explicit and implicit solvent models. This theoretical rationalization provides valuable insight into the observed regioselectivity and may be used as a predictive tool in future studies.

Graphical abstract: Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions

Supplementary files

Article information

Article type
Paper
Submitted
07 Ndz 2017
Accepted
02 Sun 2018
First published
02 Sun 2018

Org. Biomol. Chem., 2018,16, 796-806

Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions

E. B. Boydas, G. Tanriver, M. D'hooghe, H. Ha, V. Van Speybroeck and S. Catak, Org. Biomol. Chem., 2018, 16, 796 DOI: 10.1039/C7OB02253K

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