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Updated: Aug 2, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis and reactivity of a chlorinated 1,8-bis(diarylmethylium)naphthalenediyl dication
Huadong Wang1, François P Gabbaï
1Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA.
Abstract:
[Reaction: see text] 1,8-Bis(bis(p-chlorophenyl)methylium)naphthalenediyl dication has been prepared by treatment of the corresponding diol with a mixture of [HBF4]aq and (CF3CO)2O. The proximity of the methylium centers leads to strong electrostatic repulsions that are exacerbated by the electron-withdrawing p-chloro substituents. As indicated by cyclic voltammetry, this dication is the strongest oxidant of the 1,8-bis(methylium)naphthalenediyl series. It undergoes a reductive chlorination with chloride and reacts with bromide or iodide to afford the corresponding acenaphthenes.
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