Synthesis, structure and stereodynamics of atropisomeric N-chloroamides

Campbell, Aaron D. G.; Roper, Natalie J.; Waddell, Paul G.; Wills, Corinne; Dixon, Casey M.; Denton, Ross M.; Ermanis, Kristaps; Armstrong, Roly J.

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.

Citation

Campbell, A. D. G., Roper, N. J., Waddell, P. G., Wills, C., Dixon, C. M., Denton, R. M., …Armstrong, R. J. (2024). Synthesis, structure and stereodynamics of atropisomeric N-chloroamides. Chemical Communications, 60(28), 3818-3821. https://doi.org/10.1039/d4cc00268g

• Journal Article Type: Article
• Acceptance Date: Mar 7, 2024
• Online Publication Date: Mar 8, 2024
• Publication Date: Apr 11, 2024
• Deposit Date: Apr 17, 2024
• Publicly Available Date: Apr 19, 2024
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Electronic ISSN: 1364-548X
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 60
• Issue: 28
• Pages: 3818-3821
• DOI: https://doi.org/10.1039/d4cc00268g
• Keywords: Materials Chemistry; Metals and Alloys; Surfaces, Coatings and Films; General Chemistry; Ceramics and Composites; Electronic, Optical and Magnetic Materials; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/32754704
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2024/cc/d4cc00268g