2004 Fiscal Year Final Research Report Summary
The Development of A New Intramolecular Cyclization with the Organic Iron Complex
| Project/Area Number |
15550099
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka Prefectural College of Technology |
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Principal Investigator |
ITOH Keiji Osaka Prefectural College of Technology, Dept.of Industrial Systems Engineering, Professor, 総合工学システム学科, 教授 (10241225)
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| Co-Investigator(Kenkyū-buntansha) |
HIGASHIDA Suguru Osaka Prefectural College of Technology, Dept.of Industrial Systems Engineering, Assistance Professor, 総合工学システム学科, 助教授 (00208745)
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| Project Period (FY) |
2003 – 2004
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| Keywords | Organometallic Complex / Intramolecular Cyclization / Acylmetallation / Iron Complex |
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| Research Abstract |
In the presence of tetrabutylammonium tricarbonylnitrosylferrate [n-Bu_4N] [Fe(CO)_3NO] (TBAFe), 1,2-dienes (Allenes) reacted with Alkyl halides to give the corresponding (η^3-2-acylallyl) dicarbonylnitorosyliron complexes accompanied with acylmetallation. In this research, we investigate the development of the intramolecular cyclization by the reaction of ω-iodoalkylallenes with TBAFe accompanied with intramolecular acylmetallation as an advancement of the above reaction. ω-Iodoalkylallenes and TBAFe stirred at room temperature under argon for 15 h in dichloromethane and then, the reaction mixtures are chromatographed with silica gel to give the corresponding cyclic (η^3-2-acylallyl)dicarbonylnitrosyliron complexes. The yield of 5 and 6 membered rings are high and that of the 7 membered ring is very low. That of 8 membered ring is lower than that of 5 and 6 membered rings and higher than that of 7 membered ring. Then, the result cyclic π-allyliron complexes react with carbon nucleophiles at room temperature under argon in THF for 15 h. The reaction mixtures are chromatographed with silica gel to give the corresponding 2-alkyl-2-cycloalkenones in good yields. In results, a new synthetic method of some membered ring α,β-unsaturated cyclic enones is developed.
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