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

Márton Bojtár, András Simon, Petra Bombicz, and István Bitter

Organic Letters (2017)  19 (17), 4528–4531

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.

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