Issue 15, 2008
From the journal:

Chemical Communications

Mechanistic evidence for remote π-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides†

Takumi Oshima,*a   Haruyasu Asahara,a   Takuya Koizumia  and  Saki Miyamotoa  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, Japan
E-mail: oshima@chem.eng.osaka-u.ac.jp

Abstract

The acid-induced reaction of bis(p-chlorophenyl)homobenzoquinone epoxide gave the dual ipso/ortho intramolecular SE2-Ar products associated with π-aryl participated oxirane ring opening, whereas bis(p-tolyl)- and diphenyl-substituted homologues provided only the ortho products.

Graphical abstract: Mechanistic evidence for remote π-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides

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Article information

DOI
https://doi.org/10.1039/B719663F
Article type
Communication
Submitted
20 Dec 2007
Accepted
15 Feb 2008
First published
11 Mar 2008

Chem. Commun., 2008, 1804-1806

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Mechanistic evidence for remote π-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides

T. Oshima, H. Asahara, T. Koizumi and S. Miyamoto, Chem. Commun., 2008, 1804 DOI: 10.1039/B719663F

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