Issue 16, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties

Romute Yu. Garlyauskayte,*a   Andrey V. Bezdudny,a   Christophe Michot,b   Michel Armand,b   Yurii L. Yagupolskiia  and  Lev M. Yagupolskiia  

* Corresponding authors

a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02094, Murmanskaya 5, Kiev, Ukraine

b Laboratoire International sur les Matériaux Électroactifs CNRS 2289, Université de Montréal, C.P.6128, Montréal QC H3C 3J7, Canada

Abstract

N-(Trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride 4 was prepared by the oxidative fluorination of N-(trifluoromethylsulfinyl)trifluoromethanesulfonamides 3a,b which are formed by the reaction of trifluoromethyltrimethylsilane with N-(sulfinyl)trifluoromethanesulfonamide in the presence of fluoride ions. Addition of MF to N-(sulfinyl)trifluoromethanesulfonamides affords the stable N-(fluorosulfinyl)trifluoromethanesulfonamides 2a,b. Reaction of 4 with N-nucleophiles readily forms the corresponding amides 6–8.

Graphical abstract: Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties

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Article information

DOI
https://doi.org/10.1039/B205169A
Article type
Paper
Submitted
28 May 2002
Accepted
28 Jun 2002
First published
16 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1887-1889

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Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties

R. Yu. Garlyauskayte, A. V. Bezdudny, C. Michot, M. Armand, Y. L. Yagupolskii and L. M. Yagupolskii, J. Chem. Soc., Perkin Trans. 1, 2002, 1887 DOI: 10.1039/B205169A

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