Interaction of Azobenzene and Benzalaniline with Strong Amido Bases

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• 作者：Alexander N. Kornev ; Vyacheslav V. Sushev ; Natalia V. Zolotareva ; Evgenii V. Baranov ; Georgy K. Fukin ; Gleb A. Abakumov
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：17
• 期：24
• 页码：6154-6157
• 全文大小：293K
• ISSN：1523-7052

文摘

The interaction of azobenzene with lithium dicyclohexylamide (Cy₂NLi) in THF or Et₂O afforded the ion鈥搑adical 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鈥揺namido 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.