Joining the rings: the preparation of 2- and 3-indenyl-triptycenes, and curious related processes

The indenyltriptycenes, and , where the 3- or 2-indenyl, respectively, is attached at the 9-position of the triptycene, are attractive prototypes of molecular gearing systems that can also incorporate a brake. These molecules have been prepared from their respective indenylanthracenes, and , by the [4 + 2] cycloaddition of benzyne to the anthracene fragment, and the rotational barriers about the indenyl-triptycenyl single bonds in (12 kcal …