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Updated: Sep 17, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Rapid Synthesis of Naphthol Derivatives through a Photocontrolled Exothermic Process
Zhenchuang Xu1,2, Ren H Bean3, Matthew M Hausladen3
1Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States.
None:
A photocontrolled isomerization reaction of oxabenzonorbornadiene (OBNBD) derivatives with a photo acid generator (PAG) has been developed. Under irradiation, the PAG releases an acid that catalyzes the heterolytic cleavage of the benzyl ether, triggering an aromatization process accompanied by substantial heat release that accelerates the transformation. Large exotherms can further push low reactivity substrates to achieve full conversion within minutes. This approach not only illuminates practical and environmentally benign advantages in organic synthesis but also opens new avenues for developing photoresponsive molecular architectures and advanced functional materials.
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Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

