ALKYLATION AND RING CONTRACTION OF 11-OXO-6,11-DIHYDRODIBENZO[B,E]THIEPINS

The ready availability and remarkable physiological properties of a number of substituted dibenzo[b,e]thiepins have stimulated much interest in this area. The tricyclic ring system is invariably synthesized by cyclization of an o-substituted arylthiomethylbenzoic acid or acid chloride. Loss of a proton from the resulting 11-oxodibenzo[b,e]thiepin would give the mesomeric anion. This is of particular interest as the anion is fully conjugated, and 16 .pi. antiaromatic systems of this type are unknown. In addition, alkylation at C-6 would offer a rapid and direct route to a variety of substituted dibenzothiepins.