jo6b01110_si_003.cif (452.7 kB)
Conjugate Addition of 3‑Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring
dataset
posted on 2016-07-28, 00:00 authored by David R. Chisholm, Roy Valentine, Ehmke Pohl, Andrew WhitingA convenient, mild
and effective conjugate addition of 3-butyn-2-one to a variety of
anilines in ethanol is reported. The reaction was monitored and characterized
through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant
aniline-derived enaminones was explored through NMR, FTIR and X-ray
crystallography. A straightforward purification protocol that employs
direct Kugelrohr distillation was identified, and the method was further
extended to other amines and ynones, allowing rapid access to these
interesting compounds.