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Deconjugative Esterification of &alpha,&beta-Unsaturated Carboxylic Acids through Carbodiimide Coupling
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- Ichikawa Takashi
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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- Nakao Michiyasu
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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- Sano Shigeki
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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- Nagao Yoshimitsu
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
Bibliographic Information
- Other Title
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- カルボジイミド型脱水縮合剤を用いるα,β-不飽和カルボン酸の脱共役エステル化反応
Description
We have disclosed the deconjugative esterification of &alpha,&beta-unsaturated carboxylic acids through 1,3-dicyclohexylcarbodiimide (DCC) coupling. In the presence of trimethylamine hydrochloride and N,N-dimethylethylamine, an esterification of (E)-5-phenylpent-2-enoic acid and isopropanol through DCC coupling in CH2Cl2 at 50ºC afforded &beta,&gamma-unsaturated ester as a major product with a ratio of 91:9. The tendency toward deconjugation in the esterification seemed to depend on the bulkiness of alcohols. The reaction probably involves the generation of a conjugated ketene intermediate, which is converted into the corresponding &beta,&gamma-unsaturated esters by treatment with alcohols.
Journal
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- Proceedings of the Symposium on Progress in Organic Reactions and Syntheses
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Proceedings of the Symposium on Progress in Organic Reactions and Syntheses 35 (0), 108-108, 2009
Division of Organic Chemistry, The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001205635773568
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- NII Article ID
- 130006998329
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed