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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)
Author(s) -
Yoshinaga Tatsuro,
Fujiwara Takumi,
Iwata Takayuki,
Shindo Mitsuru
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904201
Subject(s) - cycloaddition , regioselectivity , halogenation , dihedral angle , yield (engineering) , benzene , silylation , chemistry , aryl , cover (algebra) , medicinal chemistry , stereochemistry , crystallography , organic chemistry , materials science , catalysis , engineering , molecule , hydrogen bond , mechanical engineering , alkyl , metallurgy
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.