First synthesis of acylated nitrocyclopropanes
Kento Iwai1,2, Rikiya Kamidate1, Khimiya Wada1
1School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
Beilstein Journal of Organic Chemistry
|June 28, 2023
Summary
This study reports the first synthesis of acyl nitrocyclopropanes. These compounds can be converted to furans, offering new synthetic pathways in organic chemistry.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Nitrocyclopropanedicarboxylic acid esters are common synthetic intermediates.
- Acyl nitrocyclopropanes have not been previously synthesized.
Purpose of the Study:
- To synthesize acyl nitrocyclopropanes.
- To explore the reactivity of these novel compounds.
Main Methods:
- Reaction of β-nitrostyrene and 1,3-dicarbonyl compounds with (diacetoxyiodo)benzene and tetrabutylammonium iodide.
- Cyclopropane synthesis via C-attack with bulkier acyl groups.
- Transformation of nitrocyclopropane to furan using tin(II) chloride.
Main Results:
- Successful synthesis of acyl nitrocyclopropanes.
- Formation of 2,3-dihydrofuran via O-attack.
- Cyclopropane formation through C-attack.
- Conversion of nitrocyclopropane to furan via ring-opening/ring-closure.
Conclusions:
- A novel synthetic route to acyl nitrocyclopropanes has been established.
- Acyl nitrocyclopropanes serve as versatile precursors for furan synthesis.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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