Superelectrophilic amidine dications: dealkylation by triflate anion

Luka S Kovacevic, Christopher Idziak, Augustinas Markevicius, Callum Scullion, Michael James Corr, Alan Kennedy, Tell Tuttle, John A Murphy

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

LanguageEnglish
Pages8516-8519
Number of pages4
JournalAngewandte Chemie International Edition
Volume51
Issue number34
Early online date13 Jul 2012
DOIs
Publication statusPublished - 20 Aug 2012

Fingerprint

Amidines
Dealkylation
anhydrides
Anions
Formamides
anions
Discrete Fourier transforms
triflic anhydride

Keywords

  • amidines
  • anions
  • cations
  • dealkylation
  • mesylates
  • methionine
  • molecular structure
  • superelectrophiles

Cite this

Kovacevic, Luka S ; Idziak, Christopher ; Markevicius, Augustinas ; Scullion, Callum ; Corr, Michael James ; Kennedy, Alan ; Tuttle, Tell ; Murphy, John A. / Superelectrophilic amidine dications : dealkylation by triflate anion. In: Angewandte Chemie International Edition . 2012 ; Vol. 51, No. 34. pp. 8516-8519.
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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 journalArticle

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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

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KW - amidines

KW - anions

KW - cations

KW - dealkylation

KW - mesylates

KW - methionine

KW - molecular structure

KW - superelectrophiles

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