Aromatic nucleophilic substitution of halobenzenes with amines under high pressure.

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概要

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• The nucleophilic substitution reactions of aromatic halides having electron-attracting groups on ortho or para position with various primary and secondary amines were accelerated by high pressure to give the corresponding <I>N</I>-substituted anilines in high yields. The bulkiness of amines affects its reactivity to lower the yields of the products. Although the secondary amines are usually less reactive than primary amines, cyclic secondary amines such as morpholine, piperidine, and pyrrolidine were found very reactive. 1,4-Diazabicyclo[2.2.2]octane and quinuclidine gave <I>N</I>-quaternary ammonium halides in high yields in contrast to the low reactivity of acyclic tertiary amines. Dichloro- and trichloro-nitrobenzenes also react with diethylamine, pyrrolidine, and morpholine to give mono-, di-, and trisubstitution products depending upon the amount of amine and the position of nitro group in these chlorides.

• 公益社団法人 日本化学会の論文

著者

• TOYODA Jiro

  Institute for Molecular Science

• Ibata Toshikazu

  Institute Of Chemistry College Of General Education Osaka University

• Isogami Yasushi

  Institute of Chemistry, College of General Education, Osaka University

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• 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.
• 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.

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