A novel route to the triphenylene ring system by a triple intramolecular acyloin condensation

Abstract

A one-pot synthesis of a sixfold functionalized dodecahydrotriphenylene 2 with D3 symmetry starting from 1,2,3,4,5,6-hexakis(eq)(ethoxycarbonylmethyl)cyclohexane (1) is described. methylsilane. The new and straightforward approach to this tetracyclic ring system is based on a triple intramolecularly occurring acyloin condensation by using sodium in the presence of chlorotriThe interest in triphenylene, hydrotriphenylenes, or substitution products thereof has been rekindled in recent years mainly due to studies on inclusion compounds"] and plate-shaped liquid crystalsp1 or the search for organic ferromagnetic materials"]. The first synthesis of such a hydrotriphenylene derivative 2, containing six oxygen functions, starting from the known hexakis-(eq)(ethoxycarbonylmethyl)cyclohexane~51 (1) is decribed here. When 1 is subjected to the conditions of the acyloin condensation by using sodium in the presence of chlorotrimethylsilane[61 2 is obtained in 53% yield.