Superelectrophilic amidine dications: dealkylation by triflate anion

Luka S Kovacevic; Christopher Idziak; Augustinas Markevicius; Callum Scullion; Michael J Corr; Alan R Kennedy; Tell Tuttle; John A Murphy

doi:10.1002/anie.201202990

Superelectrophilic amidine dications: dealkylation by triflate anion

Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8516-9. doi: 10.1002/anie.201202990. Epub 2012 Jul 13.

Authors

Luka S Kovacevic¹, Christopher Idziak, Augustinas Markevicius, Callum Scullion, Michael J Corr, Alan R Kennedy, Tell Tuttle, John A Murphy

Affiliation

¹ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

PMID: 22807275
DOI: 10.1002/anie.201202990

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amidines / chemistry*
Anions / chemistry
Cations
Dealkylation
Mesylates / chemistry*
Methionine
Molecular Structure

Substances

Amidines
Anions
Cations
Mesylates
Methionine
trifluoromethanesulfonic acid