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Updated: Aug 14, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
From pentalene to dicyclopenta[b,g]naphthalene, or the change towards delocalized structures
Inmaculada García Cuesta1, Sonia Coriani, Paolo Lazzeretti
1Instituto de Ciencia Molecular, Universidad de Valencia c/Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain. garciain@uv.es
Abstract:
Using triples-corrected coupled-cluster methods as well as other high-level theoretical approximations, the optimized parameters and isomerization barriers of the family of compounds cyclopentadiene-(benzene)x-cyclopentadiene (x = 0, 1, 2) are computed. In contrast to previous studies, s-indacene presents a localized C(2h) geometry. Also, the localized structure of pentalene is found to be the most stable, but when two benzene rings are intercalated between the five-member rings of pentalene, the resulting molecule preferably adopts a delocalized D(2h) conformation.
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