CONVENIENT HALODEAMINATION AND HYDRODEAMINATION OF PRIMARY AMINES
CONVENIENT HALODEAMINATION AND HYDRODEAMINATION OF PRIMARY AMINES
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DOI：
10.1021/jo00040a010
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发表时间：
1992-07-03
影响因子：
3.6
通讯作者：
WEI, DC
中科院分区：
文献类型：
--
作者：
GUZIEC, FS;WEI, DC
在室温下，在碱存在下，用2当量的氯胺处理伯胺的对甲苯磺酰胺，导致还原脱氨基。如果存在过量的氯胺，则以良好的产率得到相应的烷基或芳基卤化物。这两个反应大概都是通过甲苯磺酰肼和二氮烯中间体进行的;反应过程通常受空间位阻的影响。用碱和氯胺、溴或碘处理分离的甲苯磺酰肼中间体也以非常好的产率得到相应的卤化物。
Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.