Untersuchungen in der Triptycen‐Reihe, I. Synthese des Triptycens und seiner 9‐ und 9.10‐Derivate

Abstract

Aus dem Dien‐Addukt von Anthracen und p‐Benzochinon (IIa) konnte durch Reduktion mit Aluminiumisopropylat ein ungesättigtes Diol (Va) erhalten werden, das bei der Wasserabspaltung mit Phosphortrichlorid/Phosphoroxychlorid Triptycen (Ia) liefert. Auf diesem Wege ließen sich eine Reihe von in 9‐und 9.10‐Stellung substituierten Triptycenen darstellen. Aus dem unsubstituierten IIa ließen sich alle in Bezug auf den ursprünglichen Chinonring möglichen Reduktionsprodukte gewinnen.

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

“…A more efficient two-step synthesis of 15 (34%, crude) with the same starting materials by changing the reaction conditions was reported by Theilacker et al in 1960 (Scheme 4, route b). 17 The uncharacterized intermediate products of the first-step reaction were shown later (in 1998) by Yang and Swager to be a mixture of triptycene hydroquinone (22) and pentiptycene hydroquinone (23) with a poor solubility in both polar and nonpolar solvents. 18 Conversion of 23 to 15 can be readily achieved with potassium bromate in acetic acid and the overall yield was slightly larger (39% in route c of Scheme 4).…”

Merging Tribenzotriquinacene and Triptycene

“…The syn ‐adduct 23 and anti ‐adduct 22 can easily be tautomerized to the corresponding hydroquinone 26 by heating the cyclohexenediones in acetic acid in the presence of hydrogen bromide . Despite many attempts, compound 26 , which is the very first merged TBTQ‐triptycene derivative that we synthesized, did not crystallize from the various employed solvents, and because the chromatography of 26 was also difficult, we decided to use this compound as a crude intermediate.…”

Crystal structure of 5,7,12,14-tetrahydro-5,14:7,12-bis([1,2]benzeno)pentacene-6,13-dione

“…The first iptycene derivative was reported 85 years ago (Clar, 1931). Pentiptycene, first prepared by Theilacker et al (1960), is readily available from inexpensive materials and is made by Clar synthesis, which involves a Diels-Alder cycloaddition between a polycyclic diene and a benzoquinone followed by chloranil-induced dehydrogenation. Pentiptycene quinone is a precursor for pentiptycene-6,13-diol, which is subsequently used as a principal reactant for polymer synthesis.…”