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Title

Synthesis of Distorted 1,8,13‐Trisilyl‐9‐hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3‐Silylbenzynes.

Authors

Yoshinaga, Tatsuro; Fujiwara, Takumi; Iwata, Takayuki; Shindo, Mitsuru

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.

Subjects

RING formation (Chemistry); DIHEDRAL angles; CHEMICAL yield; TRIPTYCENES; HALOGENATION

Publication

Chemistry - A European Journal, 2019, Vol 25, Issue 61, p13855

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.201903024