Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively
available via a new tandem Friedel–Crafts alkylation of
tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of
5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane
gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis
acids and tetralin-1,5-diol in acetonitrile at room temperature provided the
4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new
series of perylene analogues were partially oxidized to the corresponding
contiguously aromatic, anthracene core products or fully aromatized to
3,9-dialkyloxyperylenes in good yields.
In the title compound, C26H28O2, the central atoms are coplanar, with the –CH2—CH2– links of the cyclohexene groups lying to either side of the plane and with the diallyloxy residues twisted out of this plane [C—C—O—C torsion angles = 16.6 (3) and −13.9 (3)°]. In the crystal structure, molecules are connected into chains propagating in [100] via C—H⋯π interactions.
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