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Hünlich Base: (Re)Discovery, Synthesis, and Structure Elucidation after a Century

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journal contribution
posted on 19.02.2016, 17:51 by Stephan Rigol, Lothar Beyer, Lothar Hennig, Joachim Sieler, Athanassios Giannis
After almost 100 years, the structure of the product of the reaction between 2,4-diaminotoluene and formaldehyde was elucidated: derivative 3, which we call the Hünlich base, was synthesized on a multigram scale and its enantiomers were easily separated in preparative amounts. Furthermore, transformation of the NH2 groups to the corresponding bis-iodides and bis-azides is presented. The latter was also used for desymmetrization by click chemistry.