Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 13855-13859 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 25 |
| Issue number | 61 |
| DOIs | |
| Publication status | Published - Nov 4 2019 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
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Yoshinaga, T., Fujiwara, T., Iwata, T., & Shindo, M. (2019). Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes. Chemistry - A European Journal, 25(61), 13855-13859. https://doi.org/10.1002/chem.201903024