Volume 25, Issue 61 p. 13834-13834
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Cover Feature: Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes (Chem. Eur. J. 61/2019)

Tatsuro Yoshinaga

Tatsuro Yoshinaga

Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan

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Takumi Fujiwara

Takumi Fujiwara

Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan

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Dr. Takayuki Iwata

Dr. Takayuki Iwata

Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan

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Prof. Dr. Mitsuru Shindo

Corresponding Author

Prof. Dr. Mitsuru Shindo

Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan

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First published: 24 September 2019

Graphical Abstract

Distorted triptycenes: 1,8,13-Trialkyl (aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes. More information can be found in the Communication by M. Shindo et al. on page 13855.