Superelectrophilic amidine dications: dealkylation by triflate anion.
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.
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
Luka S
LS
Kovacevic
Christopher
C
Idziak
Augustinas
A
Markevicius
Callum
C
Scullion
Michael J
MJ
Corr
Alan R
AR
Kennedy
Tell
T
Tuttle
John A
JA
Murphy
D000578:Amidines / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D002412:Cations; D003640:Dealkylation; D008698:Mesylates / Q000737:chemistry*; D008715:Methionine; D015394:Molecular Structure
D000578:Amidines; D000838:Anions; D002412:Cations; D008698:Mesylates; D008715:Methionine; C012077:trifluoromethanesulfonic acid