TY - JOUR
T1 - Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes
T2 - A New Synthetic Approach to Acenes
AU - Iwata, Takayuki
AU - Kawano, Ryusei
AU - Fukami, Takuto
AU - Shindo, Mitsuru
N1 - Funding Information:
This work was partially supported by JSPS KAKENHI (grant no. JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP20 K21198, and JP20 K15283), NAGASE Science Technology Foundation (M.S.), Asahi Glass Foundation (T.I.), Qdai‐jump Research Program Wakaba Challenge at Kyushu University (T.I.), the IRCCS Fusion Emergent Research Program (T.I.) and financial support for young researchers from IMCE, Kyushu university (T.I.). This work was performed under the Cooperative Research Program “Network Joint Research Center for Materials and Devices”.
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022/2/24
Y1 - 2022/2/24
N2 - The triptycene scaffold has been ring-opened by using a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene.
AB - The triptycene scaffold has been ring-opened by using a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene.
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U2 - 10.1002/chem.202104160
DO - 10.1002/chem.202104160
M3 - Article
C2 - 35015328
AN - SCOPUS:85124152347
SN - 0947-6539
VL - 28
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 12
M1 - e202104160
ER -