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Z. Naturforsch. 2014,
69b, 533 – 540
doi:10.5560/ZNB.2014-3271
Orthoamides and Iminium Salts LXXXV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: N, N, N′, N′-Tetraformylhydrazine and Formyl-aalen [Tris(diformylamino)methane]
Orthoamide und Iminiumsalze, LXXXV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: N,N,N′,N′-Tetraformylhydrazin und Formyl-aalen [Tris(diformylamino)methan]
1 Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany
2 Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Reprint requests to Prof. Dr. Willi Kantlehner. Fax: +49(7361)5762250. E-mail:
willi.kantlehner@htw-aalen.de
Received October 3, 2013 / published online May 7, 2014
Professor Ivo C. Ivanov zum 70. Geburtstag gewidmet
N, N, N′, N′-Tetraformylhydrazine (3) can be pepared in good yields by heating of N, N′-diformylhydrazine (5) with N, N-diformylacetamide (6). The reaction of methanesulfonyl chloride with sodium diformamide (10) in a molar ratio of 2:5 in acetonitrile affords tris(diformylamino)methane (formyl-aalen, 2). Both reactions were used to prepare 3 and 2 in large quantities (ca. 200 to 400 g). A mechanism is proposed for the formation of 2 from methanesulfonyl chloride and 10.
Key words: Large-scale Preparation, Formylating Reagents, N, N′-Diformylhydrazine, N, N-Diformylacetamide, N, N, N′, N′-Tetraformylhydrazine, Sodium Diformamide, Tris(diformylamino)methane (Formyl-aalen)