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Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism

Sonja Stanković UGent, Saron Catak UGent, Mattias D'Hooghe UGent, Hannelore Goossens UGent, Kourosch Abbaspour Tehrani, Pieter Bogaert UGent, Michel Waroquier UGent, Veronique Van Speybroeck UGent and Norbert De Kimpe UGent (2011) JOURNAL OF ORGANIC CHEMISTRY. 76(7). p.2157-2167
abstract
The synthetic utility of N-alkylidene-(2,3-dibromo-2-methylpropyl)amines and N-(2,3-dibromo-2-methylpropylidene)benzylamines was demonstrated by the unexpected synthesis of 3-methoxy-3-methylazetidines upon treatment with sodium borohydride in methanol under reflux through a rare aziridine to azetidine rearrangement. These findings stand in contrast to the known reactivity of the closely related N-alkylidene-(2,3-dibromopropyl)amines, which are easily converted into 2-(bromomethyl)aziridines under the same reaction conditions. A thorough insight into the reaction mechanism was provided by both experimental study and theoretical rationalization.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
CONVENIENT SYNTHESIS, HALOGENATED IMINO COMPOUNDS, 1-AMINO-2, 2-SUBSTITUTED PYRROLIDINES, 2-DIALKYLCYCLOPROPANECARBOXYLIC ACIDS, CHIRAL AZIRIDINES, RING TRANSFORMATION, ALPHA-CHLORO KETIMINES, CONTINUUM SOLVENT CALCULATIONS, BETA-CHLOROIMINES, HETEROCYCLIC CHEMISTRY
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
76
issue
7
pages
2157 - 2167
Web of Science type
Article
Web of Science id
000288692000020
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.45 (2011)
JCR rank
9/56 (2011)
JCR quartile
1 (2011)
ISSN
0022-3263
DOI
10.1021/jo102555r
project
HPC-UGent: the central High Performance Computing infrastructure of Ghent University
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1209382
handle
http://hdl.handle.net/1854/LU-1209382
date created
2011-04-15 08:23:39
date last changed
2013-09-17 10:46:08
@article{1209382,
  abstract     = {The synthetic utility of N-alkylidene-(2,3-dibromo-2-methylpropyl)amines and N-(2,3-dibromo-2-methylpropylidene)benzylamines was demonstrated by the unexpected synthesis of 3-methoxy-3-methylazetidines upon treatment with sodium borohydride in methanol under reflux through a rare aziridine to azetidine rearrangement. These findings stand in contrast to the known reactivity of the closely related N-alkylidene-(2,3-dibromopropyl)amines, which are easily converted into 2-(bromomethyl)aziridines under the same reaction conditions. A thorough insight into the reaction mechanism was provided by both experimental study and theoretical rationalization.},
  author       = {Stankovi\'{c}, Sonja and Catak, Saron and D'Hooghe, Mattias and Goossens, Hannelore and Tehrani, Kourosch Abbaspour and Bogaert, Pieter and Waroquier, Michel and Van Speybroeck, Veronique and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {CONVENIENT SYNTHESIS,HALOGENATED IMINO COMPOUNDS,1-AMINO-2,2-SUBSTITUTED PYRROLIDINES,2-DIALKYLCYCLOPROPANECARBOXYLIC ACIDS,CHIRAL AZIRIDINES,RING TRANSFORMATION,ALPHA-CHLORO KETIMINES,CONTINUUM SOLVENT CALCULATIONS,BETA-CHLOROIMINES,HETEROCYCLIC CHEMISTRY},
  language     = {eng},
  number       = {7},
  pages        = {2157--2167},
  title        = {Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism},
  url          = {http://dx.doi.org/10.1021/jo102555r},
  volume       = {76},
  year         = {2011},
}

Chicago
Stanković, Sonja, Saron Catak, Mattias D’Hooghe, Hannelore Goossens, Kourosch Abbaspour Tehrani, Pieter Bogaert, Michel Waroquier, Veronique Van Speybroeck, and Norbert De Kimpe. 2011. “Synthesis of 3-methoxyazetidines via an Aziridine to Azetidine Rearrangement and Theoretical Rationalization of the Reaction Mechanism.” Journal of Organic Chemistry 76 (7): 2157–2167.
APA
Stanković, Sonja, Catak, S., D’Hooghe, M., Goossens, H., Tehrani, K. A., Bogaert, P., Waroquier, M., et al. (2011). Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism. JOURNAL OF ORGANIC CHEMISTRY, 76(7), 2157–2167.
Vancouver
1.
Stanković S, Catak S, D’Hooghe M, Goossens H, Tehrani KA, Bogaert P, et al. Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism. JOURNAL OF ORGANIC CHEMISTRY. 2011;76(7):2157–67.
MLA
Stanković, Sonja, Saron Catak, Mattias D’Hooghe, et al. “Synthesis of 3-methoxyazetidines via an Aziridine to Azetidine Rearrangement and Theoretical Rationalization of the Reaction Mechanism.” JOURNAL OF ORGANIC CHEMISTRY 76.7 (2011): 2157–2167. Print.