Triptycene quinones in synthesis: preparation of triptycene cyclopentenedione and its reactivity as a dienophile |
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| Authors: | Spyroudis Spyros Xanthopoulou Nikoletta |
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| Institution: | Laboratory of Organic Chemistry, Department of Chemistry, University of Thessaloniki, Thessaloniki 54006, Greece. sspyr@chem.auth.gr |
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| Abstract: | Triptycenene quinone 1 was converted to triptycene cyclopentenedione 5 through hydroxyquinone-phenyliodonium ylide formation and thermal ring contraction of the latter. Cyclopentenedione 5 reacts as a dienophile and as a dipolarophile with dienes and nitrile oxides, affording polycyclic adducts bearing the triptycene moiety. |
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