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

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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

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Publication details

The article was received on 07 Sep 2017, accepted on 02 Jan 2018 and first published on 02 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02253K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB02253K

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