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

doi:10.1002/anie.201202990

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article

1 Citation (Scopus)

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 language	English
Pages (from-to)	8516-8519
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	51
Issue number	34
Early online date	13 Jul 2012
DOIs	https://doi.org/10.1002/anie.201202990
Publication status	Published - 20 Aug 2012

Keywords

amidines
anions
cations
dealkylation
mesylates
methionine
molecular structure
superelectrophiles

Access to Document

10.1002/anie.201202990

http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

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1 Finished

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)
Murphy, J., Coombs, G., Ferguson, A. & Florence, A.
Scottish Funding Council SFC, EPSRC (Engineering and Physical Sciences Research Council)
1/09/07 → 30/10/12
Project: Research

Cite this

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title = "Superelectrophilic amidine dications: dealkylation by triflate anion",

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.",

keywords = "amidines, anions, cations, dealkylation, mesylates, methionine, molecular structure, superelectrophiles",

author = "Kovacevic, {Luka S} and Christopher Idziak and Augustinas Markevicius and Callum Scullion and Corr, {Michael James} and Alan Kennedy and Tell Tuttle and Murphy, {John A}",

note = "Copyright {\textcopyright} 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2012",

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doi = "10.1002/anie.201202990",

language = "English",

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pages = "8516--8519",

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TY - JOUR

T1 - Superelectrophilic amidine dications

T2 - dealkylation by triflate anion

AU - Kovacevic, Luka S

AU - Idziak, Christopher

AU - Markevicius, Augustinas

AU - Scullion, Callum

AU - Corr, Michael James

AU - Kennedy, Alan

AU - Tuttle, Tell

AU - Murphy, John A

PY - 2012/8/20

Y1 - 2012/8/20

N2 - 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.

AB - 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.

KW - amidines

KW - anions

KW - cations

KW - dealkylation

KW - mesylates

KW - methionine

KW - molecular structure

KW - superelectrophiles

UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

U2 - 10.1002/anie.201202990

DO - 10.1002/anie.201202990

M3 - Article

C2 - 22807275

VL - 51

SP - 8516

EP - 8519

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 34

ER -

Superelectrophilic amidine dications: dealkylation by triflate anion

Abstract

Keywords

Access to Document

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this