Nitroacetonitrile and Its Synthetic Equivalents
Kento Iwai1,2, Nagatoshi Nishiwaki1,2
1School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
The Journal of Organic Chemistry
|August 5, 2021
Summary
Nitroacetonitrile (NAN) is an explosive reagent. A stable, soluble dipyrrolidinium salt offers a safer alternative for synthesizing complex molecules via cyano(nitro)methylation.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Nitroacetonitrile (NAN) is a valuable cyano(nitro)methylating agent.
- The explosive nature of NAN limits its practical application.
- Alkali metal salts of NAN are stable but poorly soluble in organic solvents.
Purpose of the Study:
- To develop a safer and more versatile synthetic equivalent of nitroacetonitrile.
- To enable the construction of polyfunctionalized compounds using cyano(nitro)methylation.
Main Methods:
- Synthesis and characterization of dipyrrolidinium cyano-aci-nitroacetate.
- Evaluation of its solubility and thermal stability.
- Demonstration of its utility in cyano(nitro)methylation reactions.
Main Results:
- Dipyrrolidinium cyano-aci-nitroacetate is thermally stable and soluble in common organic solvents.
- This salt effectively acts as a synthetic equivalent of nitroacetonitrile.
- It facilitates the construction of polyfunctionalized frameworks.
Conclusions:
- Dipyrrolidinium cyano-aci-nitroacetate provides a safe and practical alternative to nitroacetonitrile.
- This reagent expands the synthetic utility of cyano(nitro)methylation for creating complex molecules.
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