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

Akiko Okamoto, Ryosuke Mitsui, Shoji Watanabe, Takahiro Tsubouchi, Noriyuki Yonezawa

Department of Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan.
Departmentof Organic and Polymer Materials Chemistry,Tokyo University of Agriculture and Technology, Naka-machi, Koganei, Tokyo, Japan.

DOI: 10.4236/ijoc.2012.23029                

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.

Keywords

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

Conflicts of Interest

The authors declare no conflicts of interest.

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