Tetrahedron

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

JA Zoltewicz, NM Maier, S Lavieri, I Ghiviriga…

Index: Zoltewicz, John A.; Maier, Norbert M.; Lavieri, Sophie; Ghiviriga, Ion; Abboud, Khalil A.; Fabian, Walter M. F. Tetrahedron, 1997 , vol. 53, # 15 p. 5379 - 5388

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Citation Number: 29

Abstract

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.