Triptycene Quinones in Synthesis:  Preparation of Triptycene Cyclopentenedione and Its Reactivity as a Dienophile

Triptycene Quinones in Synthesis:  Preparation of Triptycene Cyclopentenedione and Its Reactivity as a Dienophile

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 bear...

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Veröffentlicht in:Journal of organic chemistry 2002-06, Vol.67 (13), p.4612-4614
Hauptverfasser: Spyroudis, Spyros, Xanthopoulou, Nikoletta
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020078t