Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen

Willi Kantlehner; Ioannis Tiritiris; Wolfgang Frey; Ralf Kreß

doi:10.1515/znb-2019-0230

Published by De Gruyter July 16, 2020

Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen

Orthoamides and Iminium Salts, IC. Synthesis and Reactions of N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidinium salts

Willi Kantlehner , Ioannis Tiritiris , Wolfgang Frey and Ralf Kreß

From the journal Zeitschrift für Naturforschung B

https://doi.org/10.1515/znb-2019-0230

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Abstract

Bis[bis(dibutylamino)methylen]hydrazine 8 is prepared from N,N,N′,N′-tetrabutylchloroformamidinium chloride (4c) and hydrazine. Bromine transforms 8 to the heterocyclic guanidinium salt 15a which is isolated as tetraphenylborate. From N,N,N′,N′-tetraalkylchloroformamidiniumchlorides and ethylendiamine the diguanidines are prepared which are alkylated to give diguanidinium salts, From these salts guanidinium salts can be prepared by anion metathesis with tetraphenylborate-, iodide-, hexafluorphosphate-, trifluoromethansulfonat-, bis(trifluormethansulfonyl)imide and tricyanmethanide as counteranions. The structure of the compounds 15 and 17b is confirmed by crystal structure analyses.

Keywords: alkylation; anion metathesis; diguanidines; diguanidinium salts; N,N,N′,N′-tetraalkylchlorformamidinium chlorides; N,N′-bis[bis(dibutylamino)methylene]hydrazine

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

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

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Erhalten: 2019-12-18

Angenommen: 2020-05-06

Online erschienen: 2020-07-16

Erschienen im Druck: 2020-08-27

Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen

Abstract

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