Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines

Anna Kubíčková; Athanasios Markos; Svatava Voltrová; Anežka Marková; Josef Filgas; Blanka Klepetářová; Petr Slavíček; Petr Beier

doi:10.1039/D3QO00618B

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Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines†

Anna Kubíčková,

^ab Athanasios Markos,

^a Svatava Voltrová,^a Anežka Marková,^a Josef Filgas,

^b Blanka Klepetářová,^a Petr Slavíček

^b and Petr Beier

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
E-mail: beier@uochb.cas.cz

^b University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic

Abstract

N-Fluoroalkylated 1,2,3-triazoles underwent a microwave-heating-assisted ring opening, nitrogen molecule elimination and concomitant group rearrangement to form isolable N-fluoroalkylketenimines. This reagent-free process is characterized by a wide scope and high efficiency and provides a new route to unexplored N-fluoroalkyl compounds. The reaction mechanism was investigated by a combination of mechanistic and computational studies. [2 + 2] cycloaddition of ketenimines with alkynes or alkenes afforded novel cyclobutenimines and cyclobutanimines, respectively. Addition of oxygen-, sulfur- and nitrogen nucleophiles to ketenimines gave new N-fluoroalkyl imidates, thioimidates and amidines.

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DOI: https://doi.org/10.1039/D3QO00618B
Article type: Research Article
Submitted: 25 Apr 2023
Accepted: 20 May 2023
First published: 23 May 2023
This article is Open Access

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Org. Chem. Front., 2023,10, 3201-3206

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Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines

A. Kubíčková, A. Markos, S. Voltrová, A. Marková, J. Filgas, B. Klepetářová, P. Slavíček and P. Beier, Org. Chem. Front., 2023, 10, 3201 DOI: 10.1039/D3QO00618B

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Organic Chemistry Frontiers

Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines†

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Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines

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