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Superelectrophilic amidine dications : dealkylation by triflate anion

Kovacevic, Luka S and Idziak, Christopher and Markevicius, Augustinas and Scullion, Callum and Corr, Michael James and Kennedy, Alan and Tuttle, Tell and Murphy, John A (2012) Superelectrophilic amidine dications : dealkylation by triflate anion. Angewandte Chemie International Edition, 51 (34). pp. 8516-8519. ISSN 1433-7851

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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.