Mechanistic evidence for remote pi-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides.
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.
Oshima
Takumi
T
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, 565-0871, Japan. oshima@chem.eng.osaka-u.ac.jp
Asahara
Haruyasu
H
Koizumi
Takuya
T
Miyamoto
Saki
S