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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
CO insertion in lithiated diene-tricarbonyliron complexes
Tatsuo Okauchi1, Takao Teshima, Mitsuru Sadoshima
1Department of Applied Chemistry, Kyushu Institute of Technology, 1-1, Sensui-cho, Tobata, Kitakyushu 804-8550, Japan. okauchi@che.kyutech.ac.jp
Iron complexes with lithiated dienes react with trimethyl phosphite to form new organometallic compounds. Depending on the quenching agent, either formyl or acetyl groups are introduced, yielding valuable 1,3-diene-iron complexes.
Area of Science:
- Organometallic Chemistry
- Iron Catalysis
- Organic Synthesis
Background:
- Lithiated 1,3-diene-iron complexes are versatile precursors in organometallic chemistry.
- Carbonyl insertion reactions are fundamental transformations in organometallic synthesis.
Purpose of the Study:
- To investigate the CO insertion reaction of lithiated 1,3-diene-iron complexes.
- To explore the selective synthesis of formyl and acetyl substituted diene-iron complexes.
Main Methods:
- Reaction of lithiated 1,3-diene-iron complexes with trimethyl phosphite.
- Formation of a ferrate intermediate.
- Quenching the reaction with a Brønsted acid or iodomethane.
Main Results:
- The reaction yields 3-formyl or 3-acetyl-1,3-diene-Fe(CO)(2)P(OMe)(3) complexes.
- Formylation is achieved using a strong Brønsted acid quench.
- Acetylation is achieved using iodomethane treatment.
Conclusions:
- A novel route to functionalized diene-iron complexes has been developed.
- The reaction pathway allows for selective introduction of formyl or acetyl groups.
- These findings expand the synthetic utility of iron-diene complexes.
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