Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Willi Kantlehner; Jochen Mezger; Ioannis Tiritiris; Ralf Kreß; Wolfgang Frey

doi:10.1515/znb-2020-0074

Published by De Gruyter February 4, 2021

Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Orthoamides and Iminium salts, CIII. Synthesis of N,N′,N′′-persubstituted guanidinium salt-based ionic liquids by anion metathesis

Willi Kantlehner , Jochen Mezger , Ioannis Tiritiris , Ralf Kreß and Wolfgang Frey

From the journal Zeitschrift für Naturforschung B

https://doi.org/10.1515/znb-2020-0074

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Abstract

N,N′,N′′-peralkylated guanidinium chlorides and N,N′,N′′-peralkylated guanidines were prepared from N,N′-peralkylated chloroformamidinium chlorides. The alkylation of the guanidines affords N,N′,N′′-persubstituted guanidinium chlorides bromides, iodides, alkylsulfates, and tetrafluoroborates. Guanidinium tricyanomethanides and tetracyanopropenides were prepared from the chlorides and iodides by anion metathesis. The reaction of guanidinium halogenides with borontrifluoride etherate, triethyloxonium tetrafluoroborate or sodiumtetrafluoroborate delivers guanidinium tetrafluoroborates. Guanidinium saccharinides, cyanates, thiocyanates, trifluoromethansulfonates, bis(trifluormethansulfonyl)imides, hexacyanoferrates(II/III), tetracyanonickolates and tetrathiocyanatocobaltates were prepared from the corresponding guanidinium chlorides and tetrafluoroborates by anion exchange.

Keywords: alkylation; anion metathesis; N,N′,N′′-peralkylated guanidines; N,N′,N′′-peralkylated guanidinium salts; N,N′; -peralkylated chloroformamidinium chlorides

Corresponding author: Willi Kantlehner, Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung (TOSKA), Hochschule Aalen, Beethovenstr. 1, D-73430Aalen, Germany; and Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569Stuttgart, Germany, E-mail: willi.kantlehner@hs-aalen.de

Orthoamide und Iminiumsalze CII, see ref. [1].

Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Baden-Württemberg Stiftung.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Erhalten: 2020-05-05

Angenommen: 2020-09-10

Online erschienen: 2021-02-04

Erschienen im Druck: 2021-02-23

Orthoamide und Iminiumsalze, CIII. Synthese von N,N′,N′′-peralkylierten Guanidiniumsalz-basierten ionischen Flüssigkeiten durch Anionenmetathese

Abstract

References

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