Fast Alpha Nucleophiles: Structures that Undergo Rapid Hydrazone/Oxime Formation at Neutral pH

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• 作者：Eric T. Kool ; Pete Crisalli ; Ke Min Chan
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 7, 2014
• 年：2014
• 卷：16
• 期：5
• 页码：1454-1457
• 全文大小：296K
• 年卷期：v.16,no.5(March 7, 2014)
• ISSN：1523-7052

文摘

Hydrazones and oximes are widely useful structures for conjugate formation in chemistry and biology, but their formation can be slow at neutral pH. Kinetics studies were performed for a range of structurally varied hydrazines, and a surprisingly large variation in reaction rate was observed. Structures that undergo especially rapid reactions were identified, enabling reaction rates that rival orthogonal cycloaddition-based conjugation chemistries.