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Updated: Aug 22, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1,4-Bis-(4-meth-oxy-phen-yl)naphthalene
R Manickam1, G Jagadeesan2, J Karunakaran3
1PG and Research Department of Physics, Government Arts College for Men (Autonomous), Nandanam, Chennai - 600 035, India.
Abstract:
The title naphthalene derivative, C24H20O2, features 4-methy-oxy-substituted benzene rings in the 1 and 4 positions of the naphthalene ring system. There are two crystallographically independent mol-ecules (A and B) in asymmetric unit. The independent mol-ecules have very similar conformations in which the naphthalene ring systems are only slightly bent, exhibiting dihedral angles between the constituent benzene rings of 3.76 (15) and 3.39 (15)° for A and B, respectively. The pendent 4-methyoxybenzene rings are splayed out of the plane through the naphthalene ring system to which they are connected [range of dihedral angles = 59.63 (13) to 67.09 (13)°]. In the crystal, the mol-ecular packing is consolidated by inter-molecular C-H⋯π inter-actions, leading to supra-molecular chains along the b axis. The chains assemble without directional inter-actions between them.
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