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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Sequential continuous flow processes for the oxidation of amines and azides by using HOF·MeCN
Christopher B McPake1, Christopher B Murray, Graham Sandford
1Department of Chemistry, Durham University, Durham, United Kingdom.
Chemsuschem
|December 16, 2011
Summary
This study introduces hypofluorous acid-acetonitrile (HOF·MeCN), a potent oxidizer, for continuous flow synthesis. It enables efficient nitration of amines and azides using fluorine gas, water, and acetonitrile.
Area of Science:
- Organic Chemistry
- Flow Chemistry
- Oxidation Reactions
Background:
- Hypofluorous acid-acetonitrile (HOF·MeCN) is a powerful oxidizing agent.
- Controlled generation and application of HOF·MeCN in continuous flow are challenging.
- Nitration of amines and azides often requires harsh conditions or specialized reagents.
Purpose of the Study:
- To describe the generation and use of HOF·MeCN in a controlled continuous flow process.
- To demonstrate the efficient nitration of amines and azides using this method.
- To establish a safer and more controlled approach to nitration reactions.
Main Methods:
- Utilized a single continuous flow reactor setup.
- Employed sequential gas-liquid and liquid-liquid flow procedures.
- Generated HOF·MeCN in situ using fluorine gas, water, and acetonitrile.
Main Results:
- Successfully generated and utilized HOF·MeCN in a continuous flow system.
- Achieved efficient nitration of various amines and azides to their corresponding nitrated products.
- Demonstrated the feasibility of sequential flow processes for complex oxidations.
Conclusions:
- The continuous flow generation and application of HOF·MeCN offer a controlled and efficient method for nitration.
- This approach provides a safer alternative to traditional nitration methods.
- Flow chemistry enables precise control over reactive intermediates like HOF·MeCN.
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