Diastereomers of a cofacial ternaphthalene and two azaternaphthalenes. Syntheses and barriers to isomerization

Article abstract of DOI:10.1016/S0040-4020(97)00232-9

The title compounds, a mixture of anti and syn diastereomers, were prepared by Pd-catalyzed coupling of areneboronic acids with hetaryl halides. Energy barriers for the interconversion of the diastereomers obtained by kinetic and computational studies show a dependence on the location of the annular nitrogen atom, the ortho providing a smaller barrier than the meta nitrogen atom.