iScience (Aug 2023)

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

  • Debashish Mishra,
  • Sagarika Rajkhowa,
  • Prodeep Phukan

Journal volume & issue
Vol. 26, no. 8
p. 107258

Abstract

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Summary: 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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