2003 Fiscal Year Final Research Report Summary
Insertion of Unsaturarel Organic Compounds into Carbon-Carbon Bonds
| Project/Area Number |
12450362
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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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 | KYOTO UNIVERSITY |
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Principal Investigator |
MURAKAMI Masahiro Kyoto University, Graduate School of Engineering, Professor, 工学研究科, 教授 (20174279)
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| Project Period (FY) |
2000 – 2003
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| Keywords | rhodium / cyclobutanone / carbon-carbon bond / eight-membered ring ketone / metallacycle / olefin insertion / decarbonylation |
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| Research Abstract |
Rhodium(I)-catalyzed intramolecular olefin insertion reactions of o-Styryl-substituted cyclobutanones were studied. When 3-(o-Styryl)cyclobutanone (1) was heated in m-xylene in the presence of a catalytic amount of Rh(I)-DPPE (Ph_2P(CH_2)_nPPh_2,n = 2) complex, 4-(o-styryl)-3-buten-2-one was obtained in 51% yield. The reaction of 1 in the presence of Rh(I)-DPPP (n=3) complex afforded benzobicyclo[3.2.1]octan-3-one in 81% yield. Decarbonylation of 1 occurred in the presence of Rh(I)-DPPB (n=4) complex to give 1-isopropenyl-2-vinylbenzene in 93% yield. 2-(o-Styryl)cyclobutanone underwent intramolecular olefin insertion reaction in the presence of Rh(I)-P(o-MeOC_6H_4)_3 complex to furnish eight-membered ring unsaturated ketones in 75% yield.
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