| Project/Area Number |
04640517
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | RITSUMEIKAN UNIVERSITY |
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Principal Investigator |
TANIKAGA Rikuhei Ritsumeikan University, Faculty of Sci.& Eng., Professor, 理工学部, 教授 (60025377)
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| Project Period (FY) |
1992 – 1993
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| Project Status |
Completed (Fiscal Year 1993)
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| Budget Amount *help |
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1993: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1992: ¥1,600,000 (Direct Cost: ¥1,600,000)
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| Keywords | Carboanion / Aggregation / Sulfone / Cyclopropane / Carbon-carbon bond formation / Stereoselectivity / Alkylation / 炭素-炭素結合形成 / アルキル化反応 / 立体選択的反応 / 立体反転 / スルホキシド / 炭素-炭素結合生成反応 / 光学活性化合物 |
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| Research Abstract |
The following interesting results were obtained concerning the aggregation of carbanions.
1. In dianions of beta-hydroxysulfoxides the metal counter cation of an oxyanion coordinates to the sulfinyl group, and the counter cation of a carbanion is not controlled by the sulfinyl group. Therefore, the interconversion of that carbanion readily takes place.
2. The treatment of cis- and trans- beta-alkylcyclopropy1 pheny1 sulfones with a base gives the corresponding carbaions, respectively. These carbanions undergoes the rapid interconvertion to the thermodynamically stable isomeric carbanions, and a proton or an aldehyde attacks to the carbanion to give the products. On the other hand, an alkylating reagent may attack from the other side of the anion. In the presence of an alkoxy or a 2-pyrildyl group the reaction is affected by these groups.
3. The isomeric ration of products is obtained in agreement with the MM calculation concerning the intermediary aggregation of a carbanion, a metal counter cation and THF solvent.
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