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 ก.ย. 2560
Accepted
02 ม.ค. 2561
First published
02 ม.ค. 2561

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements