Abstract:

1,2- and 1,4- additions of nucleophiles to α,β- unsaturated carbonyl compounds are among the most useful transformations in organic synthesis. 1,4-Naphthoquinones have been reported as important active compounds and are interesting substrates for studying the regioselectivity of a nucleophilic addition reaction. Lately, the ion mobility spectrometry (IMS) may become an important approach to study reaction mechanisms. Herein, we describe ESI and IMS as tools in the study of the 1,2 vs. 1,4-regioselective addition of amines to 2-bromo-1,4-naphthoquinone.