Triptycene quinones in synthesis: preparation of triptycene cyclopentenedione and its reactivity as a dienophile

Spyros Spyroudis; Nikoletta Xanthopoulou

doi:10.1021/jo020078t

Triptycene quinones in synthesis: preparation of triptycene cyclopentenedione and its reactivity as a dienophile

J Org Chem. 2002 Jun 28;67(13):4612-4. doi: 10.1021/jo020078t.

Authors

Spyros Spyroudis¹, Nikoletta Xanthopoulou

Affiliation

¹ Laboratory of Organic Chemistry, Department of Chemistry, University of Thessaloniki, Thessaloniki 54006, Greece. sspyr@chem.auth.gr

PMID: 12076168
DOI: 10.1021/jo020078t

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.