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

Unanticipated formation of symmetrical sulfonyl guanidine was observed while treating isonitriles with N,N-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...

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Autores principales: Mishra, Debashish, Rajkhowa, Sagarika, Phukan, Prodeep
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384224/
https://www.ncbi.nlm.nih.gov/pubmed/37520733
http://dx.doi.org/10.1016/j.isci.2023.107258
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author Mishra, Debashish
Rajkhowa, Sagarika
Phukan, Prodeep
author_facet Mishra, Debashish
Rajkhowa, Sagarika
Phukan, Prodeep
author_sort Mishra, Debashish
collection PubMed
description Unanticipated formation of symmetrical sulfonyl guanidine was observed while treating isonitriles with N,N-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.
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spelling pubmed-103842242023-07-30 Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine Mishra, Debashish Rajkhowa, Sagarika Phukan, Prodeep iScience Article Unanticipated formation of symmetrical sulfonyl guanidine was observed while treating isonitriles with N,N-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. Elsevier 2023-07-03 /pmc/articles/PMC10384224/ /pubmed/37520733 http://dx.doi.org/10.1016/j.isci.2023.107258 Text en © 2023 The Author(s) https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Mishra, Debashish
Rajkhowa, Sagarika
Phukan, Prodeep
Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title_full Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title_fullStr Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title_full_unstemmed Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title_short Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine
title_sort unanticipated switch of reactivity of isonitrile via n≡c bond scission: cascade formation of symmetrical sulfonyl guanidine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384224/
https://www.ncbi.nlm.nih.gov/pubmed/37520733
http://dx.doi.org/10.1016/j.isci.2023.107258
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