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

Tatsuro Yoshinaga, Takumi Fujiwara, Takayuki Iwata, Mitsuru Shindo

研究成果: ジャーナルへの寄稿記事

抄録

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.

元の言語英語
ページ(範囲)13855-13859
ページ数5
ジャーナルChemistry - A European Journal
25
発行部数61
DOI
出版物ステータス出版済み - 11 4 2019

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Halogenation
Regioselectivity
Cycloaddition
Dihedral angle
Benzene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

これを引用

Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes. / Yoshinaga, Tatsuro; Fujiwara, Takumi; Iwata, Takayuki; Shindo, Mitsuru.

:: Chemistry - A European Journal, 巻 25, 番号 61, 04.11.2019, p. 13855-13859.

研究成果: ジャーナルへの寄稿記事

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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.",
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