Structure and Reactivity of Highly Twisted N‑Acylimidazoles
journal contributionposted on 12.03.2019 by Elizabeth A. Stone, Brandon Q. Mercado, Scott J. Miller
Any type of content formally published in an academic journal, usually following a peer-review process.
A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.