5-Dibenzosuberenone is an organic chemical with use in drug synthesis. Chemically speaking, the structure can be described as a benzophenone moiety bonded through an ethylene bridge into a seven membered ring. In contrast to dibenzosuberone, dibenzosuberenone does not contain any sp3 hybridized bonds.
Dibenzosuberenone predominantly has uses in the synthesis of tricyclic antidepressants.
Dibenzosuberenone is made from dibenzosuberone by dehydrogenation.
In an alternative method dibenzosuberone is halogenated with NBS; dehydrohalogenation then also furnishes the target molecule. In an older document molecular bromine was used under irradiation. This gave a 70-90% yield of product.
2-Carboxybenzaldehyde [119-67-5] and hydroxyphthalide [16859-59-9] exist together in a tautomeric equilibrium. Wittig reaction to this forms predominantly (Z)-2-stilbenecarboxylic acid [66374-10-5]. It is important to mention that the Z-isomer is indeed the favored product of this step and not the trans-isomer. Cyclization of the carboxylic acid in polyphosphoric acid then also forms dibenzosuberenone.