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Updated: Jul 17, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Bent and Twisted: Synthesis of an Alkoxy-Substituted (1,5)Naphthalene-paracyclophanediene
Arielle Mann1, Matthew D Hannigan1, Bianca L Dumlao1
1Department of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.
Abstract:
This contribution describes the synthesis of [2.2](1,5)naphthalenoparacyclophane-1,13-diene in four steps from 1,5-bis(bromomethyl)naphthalene and 1,4-benzenedimethanethiol. Consisting of 2,6-dioctyloxynaphthalene and benzene moieties, the effects of differing arene size on the structure, strain energy, and chemical reactivity of the cyclophanediene are examined. Despite a strain energy of 24.3 kcal/mol, the naphthalenoparacyclophanediene was unreactive toward a library of olefin metathesis catalysts. This diminished reactivity can be explained by the steric hindrance of the twisted olefin. Incorporation of an electron donor (naphthalene) into the rigid paracyclophanediene structure can allow for applications in optoelectronics, chiral ligands, and planar chiral materials.
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