Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 61, Pages 13855-13859Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903024
Keywords
arynes; distortion; regioselectivity; triptycene; ynolate
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Funding
- JSPS KAKENHI [JP18H02557, JP18H04418, JP18H04624, JP17K14449]
- Asahi Glass Foundation
- Qdai-jump Research Program Wakaba Challenge at Kyushu University
- MEXT Project of Integrated Research Consortium on Chemical Sciences
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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 degrees. 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.
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