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Title: テトラアリール-o-キノジメタン:二電子還元による発生・単離と高度に歪んだ分子構造
Other Titles: Tetraaryl-o-quinodimethanes: Reductive Generation and Severely Distorted Geometry
Authors: 岩下, 新一1 Browse this author
鈴木, 孝紀2 Browse this author
Authors(alt): Iwashita, Shinichi1
Suzuki, Takanori2
Keywords: o-quinodimethane
steric repulsion
strained molecule
X-ray structure
hydrogen shift
redox system
Issue Date: Sep-2006
Publisher: 有機合成化学協会
Citation: 有機合成化学協会誌 (Journal of Synthetic Organic Chemistry Japan)
Volume: 64
Issue: 9
Start Page: 958
End Page: 968
Abstract: Introduction of four aryl groups on the highly reactive o-quinodimethane (o-QDM) skeleton suppresses the intermolecular reactivities. Thus, the unimolecular isomerization through electrocyclization is the major decomposition path for title molecules. Rational design can prevent thermal isomerization of Ar4-o-QDMs. A new general procedure to generate Ar4-o-QDM has been established here that includes two-electron reduction of the corresponding dications, whose reaction conditions no longer promote electrocyclization of Ar4-o-QDM. Several derivatives of Ar4-o-QDM with the dihydrophenanthrene, dibenzoperylene, or acenaphthene skeleton were isolated for the first time, and the details on their highly strained molecular structures were investigated by low-temperature X-ray analyses. Based on the reversible interconversion between Ar4-o-QDMs and the precursor dications, they represent a new class of electrochromic redox pairs.
Rights: ©有機合成化学協会
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 鈴木 孝紀

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