Chlorinated Polycyclic Compounds. VII. Preparation and Reactions of the Anthracene Adduct of Mucochloric Acid.

Generalization of the triptycene concept. Use of diaryne equivalents in the synthesis of iptycenes

“…A solution containing 100 mg (0.20 mmol) of 2 (R = OCH3) in 30 mL of glacial acetic acid and 10 mL of 47% hydrogen iodide was heated at reflux for 2 h. The cooled solution was extracted with chloroform, and the combined organic layers were washed successively with water, aqueous sodium bisulfite, aqueous sodium bicarbonate, and water and dried (MgS04). Removal of the solvent (rotoevaporator) left 90 mg (97%) of 2 (R = OH) as a white solid which becomes gray at about 300 °C and melts with decomposition at 427-430 °C: NMR (CDC13) 4.40 (br s, 2 ), 5.50 (s, 4 H), 6.76 (m, 8 H), 7.20 (m, 8 H); NMR (Me2SO-d6) 5.63 (s, 4 H), 6.66 (m, 8 H), 7.06 (m, 8 ), 8.40 (s, 2 H); UV (CH3OH) X^3 98 nm (log e 4.61), 278 (4.82), 262 (4.92); mass spectrum, m/e (relative intensity) 462 (74), 445 (39), 284 (32), 230 (42), 202 (100), 178 (80); IR (KBr) 3500,1470,1460,1220,750 cm™1. The compound is not very stable in air and oxidizes slowly to the corresponding quinone.…”