Practical synthesis of 9-substituted triptycene derivatives

Abstract

A series of 9-position substituted triptycene derivatives were synthesized from 9-substituted anthracenes. Diels–Alder reaction was the key reaction to form the scaffold; both benzoquinon and aryne were studied as dienophile. The diastereomers of triptycene 10a were separated by chiral high-performance liquid chromatography (HPLC) column.

Keywords:

• Anthracene
• benzene
• Diels–Alder reaction
• triptycene

Acknowledgments

The authors would like to thank Professor Zhong Li, from East China University of Science and Technology, and Professor Thomas Wirth from Cardiff University, for their help and valuable suggestions. The authors thank the School of Chemistry, Cardiff University, for support and the EPSRC National Mass Spectrometry Service Centre, Swansea, for mass spectrometric data.