The Acid-catalyzed Decomposition of α-Diazo β-Hydroxy Ketones

スポンサーリンク

概要

• 論文の詳細を見る

• The proton acid-catalyzed decomposition of 3-aryl-2-diazo-3-hydroxy-1-phenylpropanone (<B>1</B>) gave aryl and hydrogen migration products. The former was the enol-form (<B>2</B>) of 2-aryl-3-phenyl-1,3-propanedione and the latter was the enol- (<B>3</B>) and keto-form (<B>4</B>) of 1-aryl-3-phenyl-1,3-propanedione. The product ratios, <B>2</B>/(<B>3</B>+<B>4</B>), were affected by the catalysts and solvents used. More polar solvents favored the formation of aryl migration products (<B>2</B>). On the other hand, the BF<SUB>3</SUB>-catalyzed decomposition of <B>1</B> gave acetylenic ketones as main products along with <B>2</B>, <B>3</B>, and <B>4</B>. The TsOH-catalyzed decomposition of 2-diazo-3-hydroxy-3-phenyl-1-indanone, (cyclic α-diazo β-hydroxy ketone), gave 2-phenyl-1,3-indandione quantitatively through phenyl migration.

• 公益社団法人 日本化学会の論文

著者

• Ibata Toshikazu

  Institute Of Chemistry College Of General Education Osaka University

• Takebayashi Matsuji

  Department of Chemistry, Faculty of Science and Technology, Kinki University

• Takebayashi Matsuji

  Department of Chemistry, College of General Education, Osaka University

• Miyauchi Kazuo

  Department of Chemistry, Faculty of Science and Technology, Kinki University

• Hori Kimiaki

  Department of Chemistry, Faculty of Science and Technology, Kinki University

• Hirai Tsuguji

  Department of Chemistry, Faculty of Science and Technology, Kinki University

関連論文

• Nucleophilic Substitution Reaction of Aromatic Chlorides with Cyclic Tertiary Amines under High Pressure
• Formation and Reaction of Azomethine Ylide by the Reaction of Cu(acac)2-ketocarbenoids with 1,1-Diphenylmethanimine
• Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh_2(OAc)_4-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
• Molecular structure of the exo-Diels-Alder-adduct of 5-methoxy-2-methyl-4-(p-nitrophenyl)oxazole with N-methylmaleimide.
• Synthesis and molecular structure of the 2:1-cycloadduct of 1-methoxy-2-benzopyrylium-4-olate with acenaphthylene.
• The BF3 catalyzed decomposition of diazo compounds in the presence of carbonyl compounds.
• The reaction of diazo ketones in the presence of metal chelates. VIII. The stereochemistry of the 1,3-dipolar cycloaddition of 1-methoxy-2-benzopyrylium-4-olates to ethylenic dipolarophiles.
• Formation and reaction of oxazoles. Synthesis of N-substituted 2-(aminomethyl)oxazoles.
• Aromatic nucleophilic substitution of halobenzenes with amines under high pressure.
• Reaction of diazo ketones in the presence of metal chelates. VII. 1,3-Dipolar cycloaddition of 1-methoxybenzo[c]pyrylium-4-olate with acetylenic dipolarophiles.
• The acid catalyzed decomposition of diazo compounds. I. Synthesis of oxazoles in the BF3 catalyzed reaction of diazo carbonyl compounds with nitriles.
• Reactions of Diazoacetophenones in the Presence of Metal Chelates. V. Reaction of o-Methoxy-α-diazoacetophenone
• Formation of 1,3-oxathiole-2-thione and 1,2,4-trithiolane derivatives by the catalytic reaction of .ALPHA.-diazocarbonyl compounds with carbon disulfide.
• Formation and molecular structure of the 2:1-adducts of 1-alkoxy-2-benzopyrylium-4-olates with carbon disulfide.
• The Diels-Alder reactions of 2-alkyl-5-methoxy-4-(p-nitrophenyl)oxazoles with ethylenic, acetylenic, and azo-type dienophiles.
• The Acid-catalyzed Decomposition of α-Diazo β-Hydroxy Ketones
• Formation and reaction of carbonyl ylides. 1,3-Dipolar cycloaddition of 2-benzopyrylium-4-olates with carbonyl compounds.
• The high pressure Diels-Alder reactions of 5-methoxy-2-methyl-4-(p-nitrophenyl)oxazole with ethylenic dienophiles.
• The acid-catalyzed decomposition of diazo carbonyl compounds. II. Synthesis of 2- or 5-heteroatom-substituted oxazoles.
• A Betaine Intermediate in the Copper Chelate Catalyzed Decomposition of o-Methoxycarbonyl-α-diazoacetophenone

もっと見る 閉じる

スポンサーリンク