Chemospecific and Regioselective Ethereal Methyl-Oxygen Bond Cleavage Behavior of Aroylated Dimethoxynaphthalenes by Combined Action of AlCl<sub>3</sub> and Aroyl Group

Abstract

AlCl<sub>3</sub>-mediated cleavage of ethereal methyl–oxygen bond in aroylated 2,7-dimethoxynaphthalene compounds proceeds chemospecifically and regioselectively. The ethereal bond at the <i>β</i>(2)-position of 1-monoaroylated 2,7-dimethoxynaphthalene is cleaved readily and predominantly against the <i>β</i>(7)-position, whereas scission of <i>β</i>-ethereal bonds of 1,8-diaroylated 2,7-dimethoxynaphthalene hardly undergoes like the non-aroylated mother frame compound of 2,7-dimethoxynaphthalene

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

“…Conformational studies of hydroxyaryl ketones in the solid state and in solution have attracted considerable interest (Siskos et al, 2015;Nonhebel, 1968). Since the discovery of an effective method for diaroylation at the 1,8(peri)-positions of the naphthalene ring core and the related reactions (Okamoto & Yonezawa, 2009;Okamoto et al, 2011;Okamoto, Mitsui et al, 2012), we have reported on the spatial organization of 1,8-diaroylated naphthalenes and homologous compounds in both the solid state and solution Yoshiwaka et al, 2015;Okamoto et al, 2015;Ohisa et al, 2018). In the crystal structures of these compounds, which have non-coplanar accumulated aromatic rings, molecules are arranged by weak ISSN 2056-9890 intermolecular interactions, such as non-classical hydrogen bonds and van der Waals interactions.…”

“…Four compounds had an 8-benzoyl group, i.e., 1,8-diaroylated naphthalene compounds, viz. CIQBUB (Mohri et al, 2013), LESLOM (Hijikata et al, 2013), YUQBOC and YUQBOC1 (Okamoto, Mitsui et al, 2012). The remaining five compounds have a single 1-benzoyl-2-hydroxynaphthalene moiety, viz.…”

Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds

“…Based on the observation results of crystal structural analysis, the method for evaluating the actual stabilizing interactions of aromaticring-bearing molecules in solid states should be developed. The authors have investigated synthesis, reaction behavior, and analysis of spatial organization of single molecular and accumulation states of peri-aroylnaphthalene homologous compounds in which two aroyl groups are substituted at the adjacent inner carbons of the naphthalene ring [31][32][33][34], accompanying with various related compounds [35,36]. In particular, the authors have reported the crystal structures of these compounds as nearly a hundred articles.…”

Crystal structure of 7-methoxy-1-{[(E)-2,6-dimethylphenylimino] (phenyl)methyl}-2-naphthol: Clarification of non-covalent bonding interactions on the basis of spatial organization of single molecular structure and the molecular alignments

“…Recently, the authors have found highly effective diaroylation at peri (1,8)-positions of 2,7-dialkoxynaphthalene [10,11]. Furthermore, functional group interconversion of 2-and/or 7-alkoxy group to hydroxyl group is also achievable [12]. According to X-ray crystal structure analyses, the aroyl groups in these peri-aroylated naphthalene compounds are attached in a non-coplanar fashion to the naphthalene rings [13][14][15].…”