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

Author:

Kantlehner Willi1,Tiritiris Ioannis2,Frey Wolfgang2,Kreß Ralf2

Affiliation:

1. Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung (TOSKA), Hochschule Aalen, Germany und Institut für Organische Chemie , Universität Stuttgart , Pfaffenwaldring 55 , Beethovenstr. 1 , D-73430 Aalen, 70569 , Stuttgart , Germany

2. Institut für Organische Chemie , Universität Stuttgart , Pfaffenwaldring 55 , 70569 Stuttgart , Germany

Abstract

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.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

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