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Superelectrophilic amidine dications: dealkylation by triflate anion.

Angewandte Chemie (International ed. in English) (2012-07-19)
Luka S Kovacevic, Christopher Idziak, Augustinas Markevicius, Callum Scullion, Michael J Corr, Alan R Kennedy, Tell Tuttle, John A Murphy
PMID22807275
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.

MATERIALS
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