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Chemospecific and Regioselective Ethereal Methyl-Oxygen Bond Cleavage Behavior of Aroylated Dimethoxynaphthalenes by Combined Action of AlCl3 and Aroyl Group

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Author(s): Akiko Okamoto | Ryosuke Mitsui | Shoji Watanabe | Takahiro Tsubouchi | Noriyuki Yonezawa

Journal: International Journal of Organic Chemistry
ISSN 2161-4687

Volume: 02;
Issue: 03;
Start page: 194;
Date: 2012;
Original page

Keywords: Aroylated 2 | 7-Dialkoxynaphthalene; Chemospecific and Regioselective Scission of Ethereal Alkyl–Oxygen Bond; Combined Action of AlCl3 and Aroyl Group; Neighboring Group Effect

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.
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