ArticleACS omega2022
Exploring the Acid-Catalyzed Reactions of 10,11-Epoxy-Dibenzo[
Article in ACS omega, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Authors and funding
5 authors.
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Abstract
The structural diversity of polycyclic aromatic hydrocarbons (PAHs) offers exciting opportunities for their applications. Yet, selective synthesis of such conjugated networks poses a formidable challenge. Compared to the prominence of transition-metal-catalyzed cross-coupling and oxidative Scholl reactions, cationic rearrangement in the synthesis of polycyclic aromatic hydrocarbon is an underexplored subject. In this study, we reveal that cationic intermediate generated from epoxy dibenzocycloheptanol can be transformed into acenes, azulene-embedded PAHs, and dibenzocycloheptanone derivatives. Reactive patterns, including Meinwald rearrangement, Nazarov cyclization, transannular aryl migration, and transannular Friedel-Crafts cyclization were identified. Both substrate structures and reaction temperature affect the reaction pathways in predictable and manageable manners. A mechanistic scheme was postulated as the working model to guide the reactivity for further application. Substrates containing heterocyclic and ferrocenyl groups exhibit similar reactivity profiles. The inquiry culminates in the selective synthesis of 5, 7, 12, 14-tetrasubstituted
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.