TITLE:
Chemospecific and Regioselective Ethereal Methyl-Oxygen Bond Cleavage Behavior of Aroylated Dimethoxynaphthalenes by Combined Action of AlCl3 and Aroyl Group
AUTHORS:
Akiko Okamoto, Ryosuke Mitsui, Shoji Watanabe, Takahiro Tsubouchi, Noriyuki Yonezawa
KEYWORDS:
Aroylated 2, 7-Dialkoxynaphthalene; Chemospecific and Regioselective Scission of Ethereal Alkyl–Oxygen Bond; Combined Action of AlCl3 and Aroyl Group; Neighboring Group Effect
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.2 No.3,
September
25,
2012
ABSTRACT: AlCl3-mediated cleavage of ethereal methyl–oxygen bond in aroylated 2,7-dimethoxynaphthalene compounds proceeds chemospecifically and regioselectively. The ethereal bond at the β(2)-position of 1-monoaroylated 2,7-dimethoxynaphthalene is cleaved readily and predominantly against the β(7)-position, whereas scission of β-ethereal bonds of 1,8-diaroylated 2,7-dimethoxynaphthalene hardly undergoes like the non-aroylated mother frame compound of 2,7-dimethoxynaphthalene.