3, 6'-および3, 8'-ジベンゾアントロニルの合成とそれらのアルカリ縮合

芳香族多環化合物のUllmann反応に関する研究 (第5報)

抄録

The Ullmann reaction of an equimolar mixture of 3-iodobenzanthrone and 6-chlorobenzanthrone gave a new unsymmetrical compound, 3, 6'-dibenzanthronyl (8) (mp 344346°C) in 33% yield.
3, 8'-Dibenzanthronyl (9) (mp 338340°C) was obtained from 3-iodo and 8-chlorobenzanthrone in 50% yield by the same procedure. Isoviolanthrone B (4) and new violanthrone-analogue (10) (violanthrone C) were obtained in quantitative yield by alkali condensation of (8) and (9), respectively.
Hydrocarbon (12) (violanthrene C) was obtained by the reduction of (10) with zinc dust in the mixed flux of zinc chloride and sodium chloride in 66% yield, and also isoviolanthrene (11) from (4) by the same procedure in 77% yield.
The structure of (8), (9), (11) and (12) were confirmed by IR, mass spectra and elemental analysis.