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- W2124667071 abstract "Die Metallierung von 2-Pyridylmethylamin mit Dimethylzink führt in guten Ausbeuten zu Methylzink-2-pyridylmethylamid (1), das in Lösung ein Dimer-Trimer-Gleichgewicht zeigt. Verbindung 1 kristallisiert trimer mit einem Zn3N3-Cyclus in der Boot-Konformation. Die endocyclischen Zn-N-Abstände variieren von 202 bis 206 pm. Beim Erhitzen dieser Verbindung in Toluol in Anwesenheit von Dimethylzink beobachtet man die Abscheidung von Zinkmetall und die Bildung weniger Kristalle von Bis[methylzink-2-pyridylmethylamido]-N, N′-bis(methylzink)-2,3,5,6-tetrakis(2-pyridyl)-1,4-diazacyclohexan (2). Nach der mit Acetamid durchgeführten Protolyse dieses Ansatzes konnte (Z)-1-Amino-1,2-dipyridylethen (3) in Form gelblicher Kristalle in geringer Ausbeute isoliert werden. Das Enamin-Tautomere wird dabei durch N-H···N-Wasserstoffbrücken stabilisiert. Der anspruchsvolle Tris(trimethylsilyl)methyl-Rest am Zink erlaubt die Isolierung des dimeren Tris(trimethylsilyl)methylzink-2-pyridylmethylamids (4)2 in guter Ausbeute. Eine C-C-Kupplungsreaktion dieser Verbindung gelingt nicht. Metalation and C-C Coupling Reaction of 2-Pyridylmethylamine: Synthesis and Structures of Methylzinc-2-pyridylmethylamide, Tris(trimethylsilyl)methylzinc-2-pyridylmethylamide and (Z)-1-Amino-1,2-bis(2-pyridyl)ethene The metalation of 2-pyridylmethylamine with dimethylzinc yields methylzinc-2-pyridylmethylamide (1), which shows a dimer-trimer equilibrium in solution. Compound 1 crystallizes trimeric with a Zn3N3-cycle in boat conformation. The endocyclic Zn-N distances vary between 202 and 206 pm. Heating of this compound in toluene in the presence of dimethylzinc leads to the precipitation of zinc metal and to the formation of a few crystals of bis—[methylzinc-2-pyridylmethylamido]-N, N′-bis(methylzinc)-2,3,5,6—tetrakis(2-pyridyl)-1,4-diazacyclohexane (2). The protolysis of this solution with acetamide gives yellowish (Z)-1-amino-1,2-dipyridylethene (3) in a rather poor yield. The enamine tautomer is stabilized by N-H···N hydrogen bridges. The demanding tris(trimethylsilyl)methyl group at the zinc atom allows the isolation of the dimeric tris(trimethylsilyl)methylzinc-2-pyridylmethylamide (4)2 in good yield. A C-C coupling reaction of this compound with dimethylzinc is not possible." @default.
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- W2124667071 title "Metallierung und C-C-Kupplung von 2-Pyridylmethylamin: Synthese und Strukturen von Methylzink-2-pyridylmethylamid, Tris(trimethylsilyl)methylzink-2-pyridylmethylamid und (Z)-1-Amino-1,2-bis(2-pyridyl)ethen" @default.
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