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Updated: May 11, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A Flash Conversion to Aromatic Azo Compounds Expedited by Hydrazine-Trifluoroacetate Hydrogen Bonding
Yu-Meng Ye1, Hong-Wen Chen1, Huanchao Gu1
1School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong District, Shanghai 201210, China.
Abstract:
Aromatic azo compounds are very useful chemicals, but rapid and safe synthetic methods for preparing these compounds are underexplored. An extremely fast reaction was developed to prepare aromatic azo compounds from commercially available quinones and aryl hydrazinium chloride salts. The reactions could be completed within 2 min, in the presence of sodium trifluoroacetate under ambient conditions. A hydrazine-trifluoroacetate hydrogen bonding complex likely inhibited byproducts and greatly accelerated the reaction. The overall procedure is extremely simple and does not require sophisticated synthetic organic equipment and techniques.
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