Carbon-Carbon Bond Cleavage of α-Substituted Benzoins by Retro-Benzoin Condensation : A New Method of Synthesizing Ketones
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概要
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When α-benzylbenzoin (3a, α-benzyl-α-hydroxybenzyl phenyl ketone) was treated with potassium cyanide (1) in N, N-dimethylformamide at 80℃ for 1 h, the carbon-carbon bond was cleaved, resulting in the formation of deoxybenzoin (4a, benzyl phenyl ketone) and benzaldehyde (2a). This carbon-carbon bond cleavage proceeds through a retro-benzoin condensation mechanism. This mothod of synthesizing ketones was applied to several α-substituted benzoins (3), and the corresponding ketones (4) were formed in good yields. Further, we found that the cyanide ion-donating ability of tetrabutylammonium cyanide (6,Bu_4NCN) is more effective than that of potassium cyanide (1,KCN). As expected from the chemical analogy between cyanide ion and azolium ylide, serveral azolium salts (7) can also be employed in the retro-benzoin condensation as catalysts.The benzoin derivatives 3 were synthesized in the following three ways; reaction of alkyl halide (9) with benzoin (5), Michael addition of benzoin (5) with acceptors (10), and Grignard reaction of benzils (8). Alkylation of the benzoins without isolation, followed by carbon-carbon bond cleavage, readily afforded the corresponding ketones (4).
- 公益社団法人日本薬学会の論文
- 1998-01-15
著者
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Suzuki Y
School Of Pharmaceutical Sciences University Of Shizuoka
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Suzuki Y
Fukuoka Inst. Technol. Fukuoka
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Suzuki Y
Department Of Pharmacobiology And Therapeutics Faculty Of Pharmacy Meijo University
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Suzuki Y
Core Research For Evolutional Science And Technology (crest Jst) University Of Shizuoka School Of Ph
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MIYASHITA Akira
School of Pharmaceutical Sciences, University of Shizuoka
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SUZUKI Yumiko
School of Pharmaceutical Sciences, University of Shizuoka
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IWAMOTO Ken-ichi
School of Pharmaceutical Sciences, University of Shizuoka
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HIGASHINO Takeo
School of Pharmaceutical Sciences, University of Shizuoka
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OKUMURA Yoko
School of Pharmaceutical Sciences, University of Shizuoka
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Suzuki Yumiko
School Of Pharmaceutical Sciences University Of Shizuoka
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Okumura Y
School Of Pharmaceutical Sciences University Of Shizuoka
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Iwamoto K
Eisai Co. Ltd. Gifu Jpn
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Miyashita A
School Of Pharmaceutical Sciences University Of Shizuoka
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Miyashita A
Department Of Applied Chemistry Faculty Of Engineering Saitama University
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Miyashita Akira
Department Of Applied Physics School Of Engineering Nagoya University
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Miyashita Akira
School Of Pharmaceutical Sciences University Of Shizuoka
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Higashino Tt
School Of Pharmaceutical Sciences University Of Shizuoka
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Suzuki Yumiko
School Of Pharmaceutical Sciences Toho University
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Iwamoto Ken-ichi
School Of Pharmaceutical Sciences University Of Shizuoka
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