Front Cover: Retro‐Friedel‐Crafts‐Type Acidic Ring‐Opening of Triptycenes: A New Synthetic Approach to Acenes (Chem. Eur. J. 12/2022)

Abstract

The triptycene scaffold has been ring‐opened by using an acidic retro‐Friedel‐Crafts‐type reaction to give its corresponding anthrone product. 9‐Hydroxytriptycenes and unsubstituted triptycene were ring‐opened by treatment with TfOH. The electron‐donating group on the arene moiety allows the reaction to proceed in the presence of weaker acids. Additionally, the reaction has been applied toward the synthesis of tetracene. More information can be found in the Research Article by T. Iwata, M. Shindo et al. (DOI: 10.1002/chem.202104160).

3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

“…ethyl 2,2-dibromohexanoate, 16b ethyl 2,2-dibromooctanoate, 16b and 9methylanthrone 21 were synthesized according to our previous reports.…”

“…2-Methoxyfuran was purchased from Sigma-Aldrich. Ethyl 2,2-dibromopropanoate, 16b ethyl 2,2-dibromobutanoate, 16b ethyl 2,2-dibromohexanoate, 16b ethyl 2,2-dibromooctanoate, 16b and 10-methylanthrone 22 were synthesized according to our previous reports. Reaction mixtures were stirred magnetically unless otherwise noted.…”