ACID-CATALYZED REACTIONS OF N-ARYLHYDROXYLAMINES AND RELATED-COMPOUNDS WITH BENZENE - IMINIUM-BENZENIUM IONS
ACID-CATALYZED REACTIONS OF N-ARYLHYDROXYLAMINES AND RELATED-COMPOUNDS WITH BENZENE - IMINIUM-BENZENIUM IONS
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DOI：
10.1021/ja00393a025
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发表时间：
1981-01-01
影响因子：
15
通讯作者：
OKAMOTO, T
中科院分区：
文献类型：
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作者：
SHUDO, K;OHTA, T;OKAMOTO, T
N-芳基羟胺[致癌前体]在室温下与苯在三氟乙酸(TFA)存在下反应生成二苯胺。当用强酸三氟甲磺酸(TFSA)取代TFA时，主要产物为氨基联苯。通过4-取代苯羟胺和二烷基苯胺N-氧化物与苯的反应，探讨了反应的性质。反应中间体是被苯捕获得到的氨基联苯，其反应机理类似于Friedel-Craft烷基化反应。亚硝基苯和偶氮苯在强酸存在下与苯反应生成类似的产物。
N-Arylhydroxylamines [carcinogen precursors] react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines. When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls. The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene. The reactive intermediates are onium-benzenium dications which are trapped by benzene to give aminobiphenyls by a mechanism similar to the Friedel-Crafts alkylation. Nitrosobenzene and azoxybenzene reacted with benzene to give analogous products in the presence of the stronger acid.