%0 Generic
%A Chisholm, David R.
%A Valentine, Roy
%A Pohl, Ehmke
%A Whiting, Andrew
%D 2016
%T Conjugate Addition of
3‑Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights
through In Situ FTIR Monitoring
%U https://acs.figshare.com/articles/dataset/Conjugate_Addition_of_3_Buytn-2-one_to_Anilines_in_Ethanol_Alkene_Geometric_Insights_through_In_Situ_FTIR_Monitoring/3556326
%R 10.1021/acs.joc.6b01110.s003
%2 https://acs.figshare.com/ndownloader/files/5626053
%K Situ FTIR Monitoring
%K Alkene Geometric Insights
%K purification protocol
%K Conjugate Addition
%K conjugate addition
%K Kugelrohr distillation
%K NMR
%X A 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.
%I ACS Publications