Interaction of Azobenzene and Benzalaniline with Strong Amido Bases
2015
Kornev, Alexander N. | Sushev, Vyacheslav V. | Zolotareva, Natalia V. | Baranov, Evgenii V. | Fukin, Georgy K. | Abakumov, Gleb A.
The interaction of azobenzene with lithium dicyclohexylamide (Cy₂NLi) in THF or Et₂O afforded the ion–radical salt of azobenzene (1) structurally characterized for the first time and dicyclohexylaminyl radical, which begins a novel chain of transformations leading eventually to the imino–enamido lithium complex (3). Benzalaniline, being a relative of azobenzene, reacted with Cy₂NLi without electron transfer by a proton-abstraction mechanism to form the dilithium salt of N¹,N²,1,2-tetraphenylethene-1,2-diamine quantitatively.
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