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

作者信息

Oshima Takumi, Asahara Haruyasu, Koizumi Takuya, Miyamoto Saki

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, 565-0871, Japan.

出版信息

Chem Commun (Camb). 2008 Apr 21(15):1804-6. doi: 10.1039/b719663f. Epub 2008 Mar 11.

The acid-induced reaction of bis(p-chlorophenyl)homobenzoquinone epoxide gave the dual ipso/ortho intramolecular S(E)2-Ar products associated with pi-aryl participated oxirane ring opening, whereas bis(p-tolyl)- and diphenyl-substituted homologues provided only the ortho products.