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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.
Keywords
CONTINUUM SOLVENT CALCULATIONS, ACTIVATION STRAIN MODEL, DENSITY FUNCTIONALS, DISTORTION/INTERACTION ANALYSIS, NUCLEOPHILIC-SUBSTITUTION, NONCOVALENT INTERACTIONS, THERMOCHEMICAL KINETICS, CHIRAL AZIRIDINES, CYCLIC AMINES, 2-(CYANOMETHYL)AZIRIDINES

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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.
@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},
}

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