Diels-AIder Reactions of 5,5,5-Trichloro-3-penten-2-one and Related Compounds
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概要
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The Diels-AIder reaction of 5,5,5-trichloro-3-penten-2-one (<B>1a</B>) with cyclopentadiene afforded <I>exo</I>-2-acetyl-<I>endo</I>-3-trichloromethylbicyclo[2.2.1]hept-5-ene (<B>2a</B>) stereoselectively. The stereochemistry of the reactions of cyclopentadiene with several γ-chlorinated α,β-unsaturated ketones was examined. The <I>endo</I>-directive abilities decreased in the following order: CCl<SUB>3</SUB>>CCl<SUB>2</SUB>CH<SUB>3</SUB>, CHCl<SUB>2</SUB>, CCl(CH<SUB>3</SUB>)<SUB>2</SUB>>CH(CH<SUB>3</SUB>)<SUB>2</SUB>>CH<SUB>3</SUB>. Compound <B>1a</B> reacted with butadiene and furan to give 4-acetyl-5-trichloromethylcyclohexene (<B>3</B>) and 4-(2-furyl)-5,5,5-tri-chloropentan-2-one (<B>7</B>) respectively.
- 公益社団法人 日本化学会の論文
著者
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Tsuboi Sadao
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Takeda Akira
Department Of Gastroenterology Osaka General Medical Center
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Ishiguro Yasuhiro
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Tsuboi Sadao
Department of Synthetics Chemistry, School of Engineering, Okayama University
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Takeda Akira
Department of Applied Chemistry, Faculty of Engineering, Okayama University
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Ishiguro Yasuhiro
Department of Synthetics Chemistry, School of Engineering, Okayama University
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