Issue 28, 2024

Synthesis, structure and stereodynamics of atropisomeric N-chloroamides

Abstract

Atropisomeric N-chloroamides were efficiently accessed by electrophilic halogenation of ortho-substituted secondary anilides. The stereodynamics of atropisomerism in these novel scaffolds was interrogated by detailed experimental and computational studies, revealing that racemization is correlated with amide isomerization. The stereoelectronic nature of the amide was shown to significantly influence racemization rates, with potentially important implications for other C–N atropisomeric scaffolds.

Graphical abstract: Synthesis, structure and stereodynamics of atropisomeric N-chloroamides

Supplementary files

Article information

Article type
Communication
Submitted
18 Jan 2024
Accepted
07 Mar 2024
First published
08 Mar 2024
This article is Open Access
Creative Commons BY license

Chem. Commun., 2024,60, 3818-3821

Synthesis, structure and stereodynamics of atropisomeric N-chloroamides

A. D. G. Campbell, N. J. Roper, P. G. Waddell, C. Wills, C. M. Dixon, R. M. Denton, K. Ermanis and R. J. Armstrong, Chem. Commun., 2024, 60, 3818 DOI: 10.1039/D4CC00268G

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