ol9b00624_si_001.pdf (4.74 MB)

Structure and Reactivity of Highly Twisted N‑Acylimidazoles

Download (4.74 MB)
journal contribution
posted on 12.03.2019 by Elizabeth A. Stone, Brandon Q. Mercado, Scott J. Miller
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.