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异腈通过N≡C键断裂发生意外的反应性转变:对称磺酰胍的级联形成。

Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine.

作者信息

Mishra Debashish, Rajkhowa Sagarika, Phukan Prodeep

机构信息

Department of Chemistry, Gauhati University, Guwahati, Assam 781014, India.

出版信息

iScience. 2023 Jul 3;26(8):107258. doi: 10.1016/j.isci.2023.107258. eCollection 2023 Aug 18.

Abstract

Unanticipated formation of symmetrical sulfonyl guanidine was observed while treating isonitriles with -dibromoarylsulfonamides in absence of an external amine source. Interesting feature of this work is that one molecule of isonitrile initially reacts with dibromoarylsulfonamide via the C-end to produce the intermediate carbodiimide while the other molecule undergoes C≡N triple bond cleavage to react as amine source with the intermediate. This switch of reactivity from C-center to N-center of the isonitrile generated symmetrical guanidine.

摘要

在没有外部胺源的情况下,用二溴芳基磺酰胺处理异腈时,观察到意外形成了对称的磺酰胍。这项工作的有趣之处在于,一个异腈分子最初通过C端与二溴芳基磺酰胺反应生成中间体碳二亚胺,而另一个分子发生C≡N三键断裂,作为胺源与中间体反应。异腈从C中心到N中心的这种反应性转变生成了对称胍。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2102/10384224/58ea3c050c9e/fx1.jpg

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