A new method for the generation and cyclization of iminyl radicals via the Hudson reaction.

A new method for the generation and cyclization of iminyl radicals via the Hudson reaction.
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DOI:
10.1021/ol990720e
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发表时间:
1999-07
期刊:
影响因子:
5.2
通讯作者:
Xichen Lin;Didier Stien;S. Weinreb
Xichen Lin;Didier Stien;S. Weinreb
中科院分区:
化学1区
文献类型:
--
作者:
Xichen Lin;Didier Stien;S. Weinreb

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一种温和的新合成方法已被开发出来,用于原位生成亚胺基自由基并将其环化到悬垂的烯烃上,然后用各种捕获试剂中的一种将所得到的碳自由基官能化。该方法的关键过程是通过醛肟或酮肟与现成的2,6-二甲基亚砜酰氯在-50℃至室温下处理产生亚胺基自由基(Hudson反应)。
[formula: see text] A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50 degrees C to room temperature (Hudson reaction).