From the anti-tricyclo[4.2.1.12,5]deca-3,7-diene framework to 4,5,6,7-tetrachloro-isoindenone derivatives

Two formal trapping products of 4,5,6,7-tetrachloro-isoindenone (1b) can be obtained from the polycyclic precursor (4) in a multi-step sequence, thus guaranteeing the anti-orientation of the arene and alkene/arene units. Compound 2b was synthesized without the in situ generation of 4,5,6,7-tetrachloro-isoindenone 1b or cyclopentadiene and has been fully characterized. Furthermore, progress toward dibenzo derivative 3b, the poorly soluble [4+4] dimer of 1b, was made along analogous synthetic steps. In addition, the structures of two crucial intermediates were determined by X-ray crystallography.