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Experimental and Computational Insights into the Water‐Mediated Decomposition of N‐Sulfonylhydrazones: A Catalyst‐Free Synthesis of γ‐Keto/Nitrile Sulfones
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-01-30 , DOI: 10.1002/ajoc.201900728
Shagun Goyal 1 , Meenakshi Budhiraja 1 , Debasish Mandal 1 , Vikas Tyagi 1
Affiliation  

This work is an example of water‐mediated decomposition of N‐sulfonylhydrazones used as sulfonyl‐transferring reagents in the selective sulfa‐Michael reaction in the absence of any base or catalyst. A wide range of substituted N‐sulfonylhydrazones were tested as sources of sulfonyl anions with enones or acrylonitrile, which in turn provided the γ‐ keto/nitrile sulfones in very good yields. Additionally, we have performed a rigorous computational mechanistic study to investigate the role of water which demonstrates the key role of water in the hydrogen abstraction from N‐tosylhydrazone to initiate the reaction.

中文翻译:

N磺酰hydr的水介导分解的实验和计算见解:γ-酮基/腈砜的无催化剂合成

这项工作是在不存在任何碱或催化剂的情况下,在选择性磺胺-迈克尔反应中用作磺酰转移试剂的N磺酰hydr的水介导分解的一个例子。已测试了多种取代的N-磺酰基hydr作为烯酮或丙烯腈的磺酰基阴离子来源,从而以非常高的收率提供了γ-酮/腈砜。此外,我们进行了严格的计算机理研究,以研究水的作用,这证明了水在从N-甲苯磺酰zone提取氢中引发反应中的关键作用。
更新日期:2020-01-31
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