トリシクロブタベンゼンの熱的開環によるヘキサラジアレンの合成

篠崎 真也; 羽村 季之; 指宿 洋介; 鈴木 啓介

doi:10.11494/kisoyuki.2008.0.7.0

19th Symposium on Fundamental Organic Chemistry

Session ID : 1P007

DOI https://doi.org/10.11494/kisoyuki.2008.0.7.0

Conference information

Host: Organizing Committee of Symposium on Fundamental Organic Chemistry

Co-host: The Chemical Society of Japan, The Kinki Chemical Society, Japan, Osaka University Global COE Program "Global Education and Research Center for Bio-Environmental Chemistry", The Society of Synthetic Organic Chemistry, Japan, The Pharmaceutical Society of Japan

Poster Presentation

Thermal ring opening of tricyclobutabenzenes into hexaradialenes

*Shinya Shinozaki, Toshiyuki Hamura, Yousuke Ibusuki, Keisuke Suzuki

Author information

Keywords: hexaradialene, tricyclobutabenzene, thermal ring opening, steric protection

CONFERENCE PROCEEDINGS FREE ACCESS

Details

Abstract

We previously developed an efficient access to highly functionalized tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne and ketene silyl acetal. Experimental study on these strained compounds revealed that they were easily converted to the corresponding valence isomer, hexaradialene. Furthermore, it turned out that the reaction was influenced by the substituents on the four-membered ring, which is discussed in this presentation. Also discussed will be the X-ray structure of the hexaradialene.

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