Orthoamide und Iminiumsalze, CI. Umsetzungen von N,N,N′,N′-Tetramethylharnstoffdiethylacetal mit CH2-aciden Verbindungen
Author:
Kantlehner Willi12, Heckel Birgit3, Mezger Jochen1
Affiliation:
1. Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung, Hochschule Aalen , Beethovenstr. 1 , D-73430 Aalen , Germany 2. Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55 , 70569 Stuttgart , Germany 3. Fakultät Chemie/Organische Chemie, Hochschule Aalen , Beethovenstr. 1 , D-73430 Aalen , Germany
Abstract
Abstract
N,N,N′,N′-Tetramethylurea diethylacetal reacts with CH2-acidic compounds as benzylcyanide, cyanoacetic acid derivatives malonodinitrile and nitromethane to give ketene aminals or ketene-O,N-acetales. Low polar solvents favour mostly the formation of ketenaminals. The yields of ketenaminals and ketene-O,N-acetals can be improved in some cases by addition of trimethylsilyldimethylamine. The reactions of the urea acetal with diethylmalonate, ore acetyl acetone, stops at the stage of the N,N′,N″-permethylated guanidinium salts with carbanionic counterions. The formation of bis(dimethylamino)methylene-diethylmalonate from the urea acetal and diethylmalonate can be initiated by addition of trimethylsilyldimethylamine/trimethylsilylcyanide. N,N,N′,N′,N″,N″-Hexamethylguanidinium cyanide is formed in the analogous reactions of the urea acetal with N,N-dimethylcyanacetamide or diethylsuccinate. The N,N′,N″-Hexamethyl-guanidinium nitrite can be obtained from the urea acetal and nitropropane.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
Reference19 articles.
1. Kantlehner, W., Malik, H., Kreß, R. Z. Naturforsch. 2020, 75b, 697. https://doi.org/10.1515/znb-2019-0231. 2. Eine Zusammenstellung von Übersichtsartikeln findet sich unter loc. cit. [2] bei: Kantlehner W., Stieglitz R., Hauber M., Haug E., Regele C. J. Prakt. Chem. 2000, 342, 256. 3. Bredereck, H., Simchen, G., Hoffmann, H., Horn, P., Wahl, R. Angew. Chem., Int. Ed. Engl. 1967, 6, 356. https://doi.org/10.1002/anie.196703562. 4. Simchen, G., Hoffmann, H., Bredereck, H. Chem. Ber. 1963, 121, 51. 5. Simchen, G. Orthoamides: properties and reactions. In Iminium Salts in Organic Chemistry. Adv. Org. Chem.; Böhme, H., Viehe, H. G., Eds.; Wiley & Sons: New York, London, Sidney, Toronto, Vol. 9/2, 1979; p 401.
Cited by
3 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
|
|