ホモベンゾキノンエポキシドの酸触媒骨格転移反応における速度論的考察

斉藤 浩太; 浅原 時泰; 大島 巧

doi:10.11494/kisoyuki.2008.0.66.0

19th Symposium on Fundamental Organic Chemistry

Session ID : 1P066

DOI https://doi.org/10.11494/kisoyuki.2008.0.66.0

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

Kinetic Study on Acid-Mediated Rearrangement of Homobenzoquinone Epoxide

*Kota Saito, Haruyasu Asahara, Takumi Oshima

Author information

Keywords: Hammett plot, Epoxide, Acid-Mediated Rearrangement, Kinetic

CONFERENCE PROCEEDINGS FREE ACCESS

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Abstract

We investigated the acid-catalyzed skeletal rearrangement reaction of variously m-, p-substituted diaryl homoquinone epoxides. The epoxide-opening reactions was accompanied by the transannular cyclization of endo-aryl group. Both ortho and ipso transannular products were obtained. We also examined the kinetic substituent effects on these epoxide ring-opening reactions. The results indicated that the ring cleavage of epoxide involves the remote π-aryl participation.

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