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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...
The limited thermal stability of the polycyclic dione 1 can be circumvented by reacting its derivatives, hydroxyketone 3 and diol 4 with tetrachlorothiophene dioxide (6d) to yield the mono-Diels–Alder adduct 8 and rearranged polycyclic ether 11, respectively. The structures of both new products were confirmed by X-ray structure determination.
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