Abstract
Superelectrophiles: Formamides were designed that when treated with triflic anhydride would be transformed into superelectrophilic amidine dications. These dications were so electrophilic that they underwent in situ dealkylation by the triflate anion (see scheme; Tf = trifluoromethanesulfonyl). DFT calculations were used to determine the mechanistic details of the dealkylation reaction.
| Language | English |
|---|---|
| Pages | 8516-8519 |
| Number of pages | 4 |
| Journal | Angewandte Chemie International Edition |
| Volume | 51 |
| Issue number | 34 |
| Early online date | 13 Jul 2012 |
| DOIs | |
| Publication status | Published - 20 Aug 2012 |
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Keywords
- amidines
- anions
- cations
- dealkylation
- mesylates
- methionine
- molecular structure
- superelectrophiles
Cite this
}
Superelectrophilic amidine dications : dealkylation by triflate anion. / Kovacevic, Luka S; Idziak, Christopher; Markevicius, Augustinas; Scullion, Callum; Corr, Michael James; Kennedy, Alan; Tuttle, Tell; Murphy, John A.
In: Angewandte Chemie International Edition , Vol. 51, No. 34, 20.08.2012, p. 8516-8519.Research output: Contribution to journal › Article
TY - JOUR
T1 - Superelectrophilic amidine dications
T2 - Angewandte Chemie International Edition
AU - Kovacevic, Luka S
AU - Idziak, Christopher
AU - Markevicius, Augustinas
AU - Scullion, Callum
AU - Corr, Michael James
AU - Kennedy, Alan
AU - Tuttle, Tell
AU - Murphy, John A
N1 - Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2012/8/20
Y1 - 2012/8/20
N2 - Superelectrophiles: Formamides were designed that when treated with triflic anhydride would be transformed into superelectrophilic amidine dications. These dications were so electrophilic that they underwent in situ dealkylation by the triflate anion (see scheme; Tf = trifluoromethanesulfonyl). DFT calculations were used to determine the mechanistic details of the dealkylation reaction.
AB - Superelectrophiles: Formamides were designed that when treated with triflic anhydride would be transformed into superelectrophilic amidine dications. These dications were so electrophilic that they underwent in situ dealkylation by the triflate anion (see scheme; Tf = trifluoromethanesulfonyl). DFT calculations were used to determine the mechanistic details of the dealkylation reaction.
KW - amidines
KW - anions
KW - cations
KW - dealkylation
KW - mesylates
KW - methionine
KW - molecular structure
KW - superelectrophiles
UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773
U2 - 10.1002/anie.201202990
DO - 10.1002/anie.201202990
M3 - Article
VL - 51
SP - 8516
EP - 8519
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
IS - 34
ER -