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Unprecedented 1,3-tert-butyl migration via the C–N single bond scission of isonitrile: an expedient metal-free route to N-sulfonyl amidines

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Abstract

An unprecedented 1,3-migration of the tert-butyl group was observed while reacting tert-butyl isonitrile with N,N-dibromoaryl sulfonamides and nitrile. The reaction involves the simultaneous C–N single bond scission of isonitrile and the migration of the tert-alkyl group to the adjacent unsaturated nitrogen centre of the nitrile precursor, which eventually results in the formation of N-sulfonyl amidine. This method constitutes a new route for sulfonyl amidine, which does not rely on transition metals. The protocol exhibits a significant advantage in terms of substrate scope and additionally offers an easy synthesis route to guanidine molecules.

Graphical abstract: Unprecedented 1,3-tert-butyl migration via the C–N single bond scission of isonitrile: an expedient metal-free route to N-sulfonyl amidines

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Article information


Submitted
06 Apr 2020
Accepted
09 Jun 2020
First published
09 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Unprecedented 1,3-tert-butyl migration via the C–N single bond scission of isonitrile: an expedient metal-free route to N-sulfonyl amidines

D. Mishra, A. J. Borah, P. Phukan, D. Hazarika and P. Phukan, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02430A

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