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

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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.

Original languageEnglish
Pages (from-to)8516-8519
Number of pages4
JournalAngewandte Chemie International Edition
Volume51
Issue number34
Early online date13 Jul 2012
DOIs
Publication statusPublished - 20 Aug 2012

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Keywords

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

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