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Orthoamide und Iminiumsalze, LXXIV [1]. Umsetzung von N,N,N

,N

-Tetramethyl-chlorformamidiniumchlorid mit Metallen

Orthoamides and Iminium Salts LXXIV [1].

Reactions ofN,N,N,N-Tetramethyl-chloroformamidinium Chloride with Metals Willi Kantlehnera,b, Reiner Aichholzaund Martin Karla

aFakult¨at Chemie/Organische Chemie, Hochschule Aalen, Beethovenstraße 1, 73430 Aalen, Germany

bInstitut f¨ur Organische Chemie, Universit¨at Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany

Reprint requests to Prof. Dr. Willi Kantlehner. Fax: +49(7361)5762250;

E-mail: willi.kantlehner@htw-aalen.de

Z. Naturforsch.2012,67b,305 – 319; received January 5, 2012 Herrn Professor Horst Hartmann zum 75. Geburtstag gewidmet

N,N,N,N-Tetramethyl-formamidinium chloride (2a) reacts with elemental sodium in various sol- vents to giveN,N,N,N,N,N-hexamethyl-guanidinium chloride (4a). The reaction of2awith po- tassium affordsN,N,N,N,N,N,N,N-octamethyl-oxamidinium dichloride (3a). From the reac- tion of2awith magnesium in different solvents in general result mixtures of the salts4a, 3aand N,N,N,N-tetramethyl-formamidinium chloride (10a). The composition of these mixtures depends on the solvent and the reaction temperature. Similar results are obtained, when a zinc/copper couple is used instead of magnesium. Very likely from2aand magnesium or zinc, respectively, organometallic intermediates11,12are formed which could be trapped by aromatic aldehydes and phenylisocyana- te. The salt2acan be reductively coupled by a low-valent titanium reagent to give the oxamidinium salt3a.

Key words:Iminium Salts, Chloroformamidinium Salts, Organometallic Compounds (Mg, Zn), Oxamidinium Salts, Nucleophilic Carbenes, Aromatic Aldehydes,

Mandelic Acid Amides

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