Benzyltriefhylamthoniurn Hydroxide-catalyzed Formation of α, α'-Dichloro p, p'-dinitrostilbene from i-Nitrobenzyl Chloride in the Mixture of Carbon Tetrachloride and Nitrobenzene

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Other Title
  • 四塩化炭素-ニトロベンゼン混合溶媒中におけるベンジルトリエチルアンモニウム=ヒドロキシド触媒によるP-ニトロベンジル=クロリドよりのα,α'-ジクロロ-P,P'-ジニトロスチルベンの生成
  • 塩基触媒反応　Ｖ　　四塩化炭素‐ニトロベンゼン混合溶媒中におけるベンジルトリエチルアンモニウム・ヒドロキシド触媒によるｐ‐ニトロベンジルクロリドよりのα，α′‐ジクロル‐ｐ，ｐ′‐ジニトロスチルベンの生成

Description

Treatment of p-nitrobenzyl chloride with benzyltriethylammonium hydroxide in the mixture of carbon tetrachloride and nitrobenzene was found to give a, a'-dichloro-p, p'-dinitrostilbene [3] in a 98% yield under the most favorable condition. Bis(p-nitrophenyl)acethylene C2C and p, p'-dinitrostilbene [1] were obtained as byproducts. The yield of C3 J varied considerably with the molar ratio of nitrobenzene to carbon tetrachloride; in the the absence of nitrobenzene [3] was formed in a 25% yield, while in the absence of carbon tetrachloride [3] was not formed at all. The most favorable medium employed for the formatiom of [3] was found to be a 2: 1 mixture of nitrobenzene and carbon tetrachloride. Furthermore, C 3D was also obtained from p-nitrotoluene or nitrobenzene in the presence of carbon tetrachloride under similar conditions, and the formation of chloroform and hexachloroethane was confirmed in the reaction products.<BR>These results suggest that the reaction proceeds through a radical mechanism, and provide strong support for the chlorine atom in a-position of [3] coming from carbon tetrachloride.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1974 (11), 2127-2131, 1974-11-10

    The Chemical Society of Japan

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