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Issue 8, 2009
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New kinds of organic superacids. Bis(perfluoroalkylsulfonylimino)trifluoromethanesulfonic acids and their trimethylsilyl esters

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Abstract

A synthesis of new unsymmetric trifluoromethylsulfonylimino(nonafluoro-n-butyl-sulfonylimino)trifluoromethanesulfonic acid (1b) is reported. During the silylation reactions studies of bis(perfluoroalkylsulfonylimino)trifluoromethanesulfonic acids (1a,b) it was shown that reaction proceeds exclusively on the central oxygen atom to give trimethylsilyl esters. The obtained esters along with several trimethylsilylesters of sulfonic acids have been studied by 29Si-NMR spectroscopy and an attempt to estimate the strength of bis(perfluoroalkylsulfonylimino)trifluoromethanesulfonic acids by the 29Si-NMR chemical shifts of their trimethylsilylesters was made, resulting in the conclusion that these compounds may be cited as the strongest organic Brønsted acids.

Graphical abstract: New kinds of organic superacids. Bis(perfluoroalkylsulfonylimino)trifluoromethanesulfonic acids and their trimethylsilyl esters

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Supplementary files

Article information


Submitted
01 Sep 2008
Accepted
12 Jan 2009
First published
04 Mar 2009

Org. Biomol. Chem., 2009,7, 1642-1645
Article type
Paper

New kinds of organic superacids. Bis(perfluoroalkylsulfonylimino)trifluoromethanesulfonic acids and their trimethylsilyl esters

A. G. Posternak, R. Yu. Garlyauskayte, V. V. Polovinko, L. M. Yagupolskii and Y. L. Yagupolskii, Org. Biomol. Chem., 2009, 7, 1642
DOI: 10.1039/B815155E

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