1990 Fiscal Year Final Research Report Summary
Development of New Methods Synthesis of Nonbenzenoid Aromatic Compounds Utilizing Electrochemical Reaction
| Project/Area Number |
63430018
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| Research Category |
Grant-in-Aid for General Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
SHONO Tatsuya Kyoto University, Faculty of Engineering, Professor, 工学部, 教授 (80025858)
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| Co-Investigator(Kenkyū-buntansha) |
KISE Naoki Kyoto University, Faculty of Engineering, Assistant Professor, 工学部, 助手 (90177824)
KASHIMURA Shigenori Kyoto University, Faculty of Engineering, Assistant Professor, 工学部, 助手 (50152632)
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| Project Period (FY) |
1988 – 1990
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| Keywords | Cycloheptatrienes / Electrochemical Reactions / Nonbenzenoid Aromatic Compounds |
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| Research Abstract |
In this project, development of new methods for the synthesis of nonbenzenoid aromatic Compounds has been studied utilizing electrochemical reactions. Following results were obtained in this project.
1. Efficient method for the introduction of alkyl groups at alpha-position of tropone ring has been established by using anodic oxidation of cycloheptatrienes as a key reaction, and it was applied to the facile synthesis of naturally occurring alpha-thujaplicin.
2. New method for the preparation of 4-alkylsubstituted tropones has been exploited by the reaction of RLi with 7,7-dimethoxycycloheptatriene which was easily prepared by the anodic oxidation of 3-methoxy-cycloheptatriene. By utilizing this new method, the preparation of nezukone was attained. In addition, regioselective acylation of cyclo= heptatriene systems was also established.
3. Electroreductive coupling of cycloheptatriene systems with ketones and alkyl halides was found to be regioselective, and these reactions were proved to be useful for the propara-tion of 3-substituted tropones and hydroazulen skeletons. The simple methods for the syntheses of hinokitiol and betadolablin were established by using this reaction.
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Research Products
(9 results)
