Expanding the Pillararene Chemistry: Synthesis and Application of a 10 + 1 Functionalized Pillar[5]arene

A novel
functionality was introduced in the pillararene family
by the Claisen rearrangement of monoallyl pillar[5]­arene. This new
key derivative can lead to the formation of a 10 + 1 functionalized
derivative, a useful scaffold for further derivatization. Except for
the previously known monodeprotection reaction, all steps proceed
efficiently with high yields and easy separation. In addition, a solvent-responsive
pseudo[1]­rotaxane was synthesized based on this novel functionality.