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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
2,7-Dimeth-oxy-1,8-bis-(4-phen-oxy-benzo-yl)naphthalene
Daichi Hijikata1, Teruhisa Takada, Atsushi Nagasawa
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan.
Abstract:
In the title mol-ecule {systematic name: [2,7-dimethoxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methan-one}, C(38)H(28)O(6), the 4-phen-oxy-benzoyl units adopt a syn orientation with respect to the naphthalene ring system. The inter-nal benzene rings, A and B, make dihedral angles of 86.72 (5) and 79.22 (5)° with the naphthalene ring system. The two terminal benzene rings, C and D, of the 4-phen-oxy-benzoyl groups are twisted with respect to benzene rings A and B, with dihedral angles of A/C = 62.72 (8) and B/D = 87.61 (6)°. In the crystal, H atoms in the naphthalene system make two types of inter-molecular C-H⋯O inter-actions with the carbonyl O atom and the phenyl etheral O atom of neighbouring mol-ecules. Mol-ecules are further linked by C-H⋯π inter-actions involving a H atom of terminal benzene ring D and the π-system of the inter-nal benzene ring A, forming dimers centered about an inversion center.
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