TRIPTYCENE-LIKE BEHAVIOUR OF TERTIARY 9,10-DIHYDRO-9-ANTHROLS

Article abstract of DOI:10.1016/0040-4039(81)89002-8

Secondary alcohols in the 9,10-dihydro-9-anthrol series frequently undergo acid-catalyzed elimination and substitution reactions more rapidly than do corresponding tertiary alcohols - a phenomenon attributed to predominant existence of the tertiary alcohols in triptycene-like conformations with the hydroxy groups in pseudoequatorial positions.