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Toward calix[2]-type macrocycles: Synthesis and structural analysis of cyclic tetraketone and highly strained furanophane

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Title: Toward calix[2]-type macrocycles: Synthesis and structural analysis of cyclic tetraketone and highly strained furanophane
Authors: Sano, Taichi Browse this author
Sun, Yuhua Browse this author
Mukai, Taichi Browse this author
Inaba, Yuya Browse this author
Yoneda, Tomoki Browse this author →KAKEN DB
Ide, Yuki Browse this author →KAKEN DB
Pirillo, Jenny Browse this author
Hijikata, Yuh Browse this author →KAKEN DB
Inokuma, Yasuhide Browse this author →KAKEN DB
Keywords: calixpyrrole
strained macrocycle
Issue Date: Jul-2023
Publisher: World Scientific Publishing
Journal Title: Journal of porphyrins and phthalocyanines
Volume: 27
Issue: 07n10
Start Page: 1067
End Page: 1073
Publisher DOI: 10.1142/S1088424623500189
Abstract: Recent progress in the synthesis of calix[3]pyrrole has proven that cyclic polyketones composed of 3,3-dialkylated pentane-2,4-diones as the repeating unit are promising precursors for strained calix-type macrocycles. Toward the synthesis of calix[2]pyrrole and calix[2]furan, which are the most strained congeners among the possible calix[n]pyrroles and calix[n]furans, we report the synthesis of a cyclic dimer of 3,3-dimethylpentane-2,4-dione and its furanophane derivative. These compounds were produced from a linear tetraketone precursor. Single crystal X-ray diffraction analysis revealed that the furan ring in the furanophane was highly strained with deformation angles alpha and beta of 3.69 degrees and 16.00 degrees, respectively. These deformation angles were the largest in the series of 1,4-diketone-linked oligofuran macrocycles. Although these two macrocyclic compounds are likely the most promising precursors for calix[2]-type macrocycles, Paal-Knorr-type pyrrole or furan ring formation did not proceed under standard conditions used for calix[3]pyrrole or calix[3]furan. Theoretical calculations indicated that the second aromatic ring formation on the cyclic tetraketone is a highly uphill process whose activation energy cannot be overcome by standard thermal reactions.
Rights: Electronic version of an article published as Journal of Porphyrins and Phthalocyanines, Vol. 27, No. 07n10, pp. 1067-1073 (2023), 10.1142/S1088424623500189, copyright© World Scientific Publishing Company,
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 猪熊 泰英

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