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Solvent-controlled selective transformation of 2-Bromomethyl-2-methylaziridines to functionalized Aziridines and Azetidines

Sonja Stanković UGent, Hannelore Goossens UGent, Saron Catak UGent, Meniz Tezcan UGent, Michel Waroquier UGent, Veronique Van Speybroeck UGent, Matthias D'hooghe UGent and Norbert De Kimpe UGent (2012) JOURNAL OF ORGANIC CHEMISTRY. 77(7). p.3181-3190
abstract
The reactivity of 2-bromomethyl-2-methylaziridines toward oxygen, sulfur, and carbon nucleophiles in different solvent systems was investigated. Remarkably, the choice of the solvent has a profound influence on the reaction outcome, enabling the selective formation of either functionalized aziridines in dimethylformamide (through direct bromide displacement) or azetidines in acetonitrile (through rearrangement via a bicyclic aziridinium intermediate). In addition, the experimentally observed solvent-dependent behavior of 2-bromomethy1-2-methylaziridines was further supported by means of DFT calculations.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
THEORETICAL RATIONALIZATION, THERMODYNAMIC FUNCTIONS, RING TRANSFORMATION, SYNTHETIC APPLICATIONS, CHIRAL AZIRIDINES, MIXED-SOLVENTS, SINGLE IONS, AB-INITIO, REARRANGEMENT, DERIVATIVES
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
77
issue
7
pages
3181 - 3190
Web of Science type
Article
Web of Science id
000302388000015
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.564 (2012)
JCR rank
9/55 (2012)
JCR quartile
1 (2012)
ISSN
0022-3263
DOI
10.1021/jo202637a
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2094904
handle
http://hdl.handle.net/1854/LU-2094904
date created
2012-04-26 11:50:02
date last changed
2013-04-06 00:30:38
@article{2094904,
  abstract     = {The reactivity of 2-bromomethyl-2-methylaziridines toward oxygen, sulfur, and carbon nucleophiles in different solvent systems was investigated. Remarkably, the choice of the solvent has a profound influence on the reaction outcome, enabling the selective formation of either functionalized aziridines in dimethylformamide (through direct bromide displacement) or azetidines in acetonitrile (through rearrangement via a bicyclic aziridinium intermediate). In addition, the experimentally observed solvent-dependent behavior of 2-bromomethy1-2-methylaziridines was further supported by means of DFT calculations.},
  author       = {Stankovi\'{c}, Sonja and Goossens, Hannelore and Catak, Saron and Tezcan, Meniz and Waroquier, Michel and Van Speybroeck, Veronique and D'hooghe, Matthias and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {THEORETICAL RATIONALIZATION,THERMODYNAMIC FUNCTIONS,RING TRANSFORMATION,SYNTHETIC APPLICATIONS,CHIRAL AZIRIDINES,MIXED-SOLVENTS,SINGLE IONS,AB-INITIO,REARRANGEMENT,DERIVATIVES},
  language     = {eng},
  number       = {7},
  pages        = {3181--3190},
  title        = {Solvent-controlled selective transformation of 2-Bromomethyl-2-methylaziridines to functionalized Aziridines and Azetidines},
  url          = {http://dx.doi.org/10.1021/jo202637a},
  volume       = {77},
  year         = {2012},
}

Chicago
Stanković, Sonja, Hannelore Goossens, Saron Catak, Meniz Tezcan, Michel Waroquier, Veronique Van Speybroeck, Matthias D’hooghe, and Norbert De Kimpe. 2012. “Solvent-controlled Selective Transformation of 2-Bromomethyl-2-methylaziridines to Functionalized Aziridines and Azetidines.” Journal of Organic Chemistry 77 (7): 3181–3190.
APA
Stanković, Sonja, Goossens, H., Catak, S., Tezcan, M., Waroquier, M., Van Speybroeck, V., D’hooghe, M., et al. (2012). Solvent-controlled selective transformation of 2-Bromomethyl-2-methylaziridines to functionalized Aziridines and Azetidines. JOURNAL OF ORGANIC CHEMISTRY, 77(7), 3181–3190.
Vancouver
1.
Stanković S, Goossens H, Catak S, Tezcan M, Waroquier M, Van Speybroeck V, et al. Solvent-controlled selective transformation of 2-Bromomethyl-2-methylaziridines to functionalized Aziridines and Azetidines. JOURNAL OF ORGANIC CHEMISTRY. 2012;77(7):3181–90.
MLA
Stanković, Sonja, Hannelore Goossens, Saron Catak, et al. “Solvent-controlled Selective Transformation of 2-Bromomethyl-2-methylaziridines to Functionalized Aziridines and Azetidines.” JOURNAL OF ORGANIC CHEMISTRY 77.7 (2012): 3181–3190. Print.