tert-Butyl-N-chlorocyanamide: A Novel and Versatile Reagent in Organic Synthesis
tert-Butyl-N-chlorocyanamide: A Novel and Versatile Reagent in Organic Synthesis
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叔丁基-N-氯氰酰胺：一种新型多功能有机合成试剂
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发表时间：
2007
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通讯作者：
M. P. Kaushik
中科院分区：
文献类型：
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作者：
Vinod Kumar;M. P. Kaushik
本文讨论了叔丁基-N-氯氰酰胺的化学性质及其在各种有机转化反应中的应用。该试剂在有机合成中的氯化和氧化反应中具有很高的通用性。叔丁基-N-氯氰酰胺具有反应性，并具有高活性氯含量;它也是安全的，可溶于所有有机溶剂，可回收利用。该试剂就其活性氯含量而言在环境条件下稳定两年以上。叔丁基-N-氯氰酰胺能够产生高水平的正氯，这主要是其参与许多有用的有机转化的原因，包括硫化物转化为亚砜，酮肟转化为偕-氯亚硝基化合物，醛肟转化为羟肟酰氯和2-异恶唑啉，二烷基和二芳基亚磷酸酯转化为二烷基和二芳基氯磷酸酯，仲醇转化为酮，以及硫醇偶联生成二硫化物和硫芥（一种化学战剂）及其模拟物的氧化去污。此外，该试剂可经历与各种烯烃的光解加成。
The chemistry and applications of tern-butyl-N-chlorocyanamide in a variety of organic transformations is discussed in this account. The reagent was found to be highly versatile for chlorination and oxidation reactions in organic synthesis. tert-Butyl-N-chlorocyanamide is reactive and possesses a high active chlorine content; it is also safe, soluble in all organic solvents, and recyclable. The reagent is stable, in terms of its active chlorine content, under ambient conditions for a period of more than two years tert-Butyl-N-chlorocyanamide is able to generate a high level of positive chlorine that is mainly responsible for its involvement in many useful organic transformations, including the conversion of sulfides into sulfoxides, ketoximes into gem-chloronitroso compounds, ald-oximes into hydroximoyl chlorides and 2-isoxazolines, dialkyl and diaryl phosphites into dialkyl and diaryl chlorophosphates, and secondary alcohols into ketones, as well as the coupling of thiols to give disulfides and the oxidative decontamination of sulfur mustard (a chemical warfare agent) and its simulants. In addition, the reagent can undergo photolytic addition to various olefins.