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

Esma B Boydas, Gamze Tanriver, Matthias D'hooghe UGent, Hyun-Joon Ha, Veronique Van Speybroeck UGent and Saron Catak UGent (2018) ORGANIC & BIOMOLECULAR CHEMISTRY. 16(5). p.796-806
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
CONTINUUM SOLVENT CALCULATIONS, ACTIVATION STRAIN MODEL, DENSITY FUNCTIONALS, DISTORTION/INTERACTION ANALYSIS, NUCLEOPHILIC-SUBSTITUTION, NONCOVALENT INTERACTIONS, THERMOCHEMICAL KINETICS, CHIRAL AZIRIDINES, CYCLIC AMINES, 2-(CYANOMETHYL)AZIRIDINES
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
16
issue
5
pages
796 - 806
Web of Science type
Article
Web of Science id
000423787600017
ISSN
1477-0520
1477-0539
DOI
10.1039/c7ob02253k
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8562412
handle
http://hdl.handle.net/1854/LU-8562412
date created
2018-05-22 08:45:01
date last changed
2018-05-24 11:59:56
@article{8562412,
  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.},
  author       = {Boydas, Esma B and Tanriver, Gamze and D'hooghe, Matthias and Ha, Hyun-Joon and Van Speybroeck, Veronique and Catak, Saron},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {CONTINUUM SOLVENT CALCULATIONS,ACTIVATION STRAIN MODEL,DENSITY FUNCTIONALS,DISTORTION/INTERACTION ANALYSIS,NUCLEOPHILIC-SUBSTITUTION,NONCOVALENT INTERACTIONS,THERMOCHEMICAL KINETICS,CHIRAL AZIRIDINES,CYCLIC AMINES,2-(CYANOMETHYL)AZIRIDINES},
  language     = {eng},
  number       = {5},
  pages        = {796--806},
  title        = {Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions},
  url          = {http://dx.doi.org/10.1039/c7ob02253k},
  volume       = {16},
  year         = {2018},
}

Chicago
Boydas, Esma B, Gamze Tanriver, Matthias D’hooghe, Hyun-Joon Ha, Veronique Van Speybroeck, and Saron Catak. 2018. “Theoretical Insight into the Regioselective Ring-expansions of Bicyclic Aziridinium Ions.” Organic & Biomolecular Chemistry 16 (5): 796–806.
APA
Boydas, E. B., Tanriver, G., D’hooghe, M., Ha, H.-J., Van Speybroeck, V., & Catak, S. (2018). Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions. ORGANIC & BIOMOLECULAR CHEMISTRY, 16(5), 796–806.
Vancouver
1.
Boydas EB, Tanriver G, D’hooghe M, Ha H-J, Van Speybroeck V, Catak S. Theoretical insight into the regioselective ring-expansions of bicyclic aziridinium ions. ORGANIC & BIOMOLECULAR CHEMISTRY. 2018;16(5):796–806.
MLA
Boydas, Esma B, Gamze Tanriver, Matthias D’hooghe, et al. “Theoretical Insight into the Regioselective Ring-expansions of Bicyclic Aziridinium Ions.” ORGANIC & BIOMOLECULAR CHEMISTRY 16.5 (2018): 796–806. Print.