1989 Fiscal Year Final Research Report Summary
Novel Carbon-Carbon Bond Formation Utilizing Selective C-H Bond Insertion by Carbenes.
| Project/Area Number |
63470080
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto Institute of Technology |
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Principal Investigator |
OKU Akira Kyoto Institute of Technology, Department of Chemistry, Professor., 工芸学部, 教授 (50027885)
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| Co-Investigator(Kenkyū-buntansha) |
KAMADA Tohru Kyoto Institute of Technology, Department of Chemistry, Assistant., 工芸学部, 助手 (30214513)
HARADA Toshiro Kyoto Institute of Technology, Department of Chemistry, Associate Professor., 工芸学部, 助教授 (30135628)
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| Project Period (FY) |
1988 – 1989
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| Keywords | carbene / carbenoid / C-H insertion / organic synthesis / cyclopropanol / electron transfer / oxonium ylide |
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| Research Abstract |
1988: (1) Optimized reaction conditions for regioselective C-H insertion or alkoxides by a variety of carbenes were examined. (2) In addition to alkoxides, other substrates which undergo selective insertion by carbenes were investigated. Enolate anion, nitrile carbanion, and alkyllithium were found to undergo selective - C-H insertion.
1989: (3) Promotion effect of t-BuOK on the reaction of bromolithiocarbenoids at low temperatures was found and their reactivity as carbene sources was investigated. (4) Reaction of cyclopropanol derivatives such as cyclopropanone hemiacetals and cyanohydrins with unencumbered carbenes yielded novel ring-opened cycloadduct propionates in high yields. (5) A novel-type of three-component joint reactions between cyclic etliercarbene - nucleophile was investigated to find that the formation of oxonium ylide intermediate is the key step of this reaction.
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