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Anthraquinodimethane Ring-Flip in Sterically Congested Alkenes: Isolation of Isomer and Elucidation of Intermediate through Experimental and Theoretical Approach

Bulletin of the Chemical Society of Japan, ISSN: 1348-0634, Vol: 95, Issue: 1, Page: 38-46
2022
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Article Description

From the viewpoint of the development of molecular response systems, stimulus-induced switching of multiconformational/multi-configurational overcrowded ethylenes are interesting, whose properties could be manipulated by understanding the detailed isomerization paths. Anthraquinodimethane (AQD) ring-flip is usually a very fast process, and thus less studied experimentally. Herein, we studied AQDs with dibenzo- and tribenzocycloheptatrienylidene units, which have large enough steric hindrance to retard the AQD ring-flip to allow determination of the ¦Gvalue experimentally. Their thermal isomerization was also scrutinized using the artificial force induced reaction method to elucidate the intermediates. Based on the structural unsymmetry in a newly prepared AQD, one of the isomers that undergoes a reversible conformational change via AQD ring-flip was isolated and analyzed by X-ray for the first time.

Bibliographic Details

Yusuke Ishigaki; Tomoki Tadokoro; Yu Harabuchi; Yuki Hayashi; Satoshi Maeda; Takanori Suzuki

Oxford University Press (OUP)

Chemistry

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