%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