Synthesis of Distorted 1, 8, 13‐Trisilyl‐9‐hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3‐Silylbenzynes. Issue 61 (28th August 2019)

• Record Type: Journal Article
• Authors: Yoshinaga, Tatsuro; Fujiwara, Takumi; Iwata, Takayuki; Shindo, Mitsuru
• Is Part Of: Chemistry. Volume 25:Issue 61(2019)
• Page Start: 13855
• Page End: 13859
• Publication Date: 2019-08-28
• Subjects: arynes -- distortion -- regioselectivity -- triptycene -- ynolate; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903024
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Regioselectivity : 1, 8, 13‐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 were as high as 35°. The distortion energy induced step‐by‐step halogenation reactions to yield halogenated triptycenes, which were converted to 1, 8, 13‐functionalized triptycenes.