Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?
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Date
2021-09Type
- Journal Article
Abstract
Three novel thiol bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, disulfide chemistry, and Bronsted acid catalysis. This work demonstrates that (1) one aromatic thiol on the resorcin[4]arene framework is tolerated in the self-assembly process to a hexameric hydrogen bond-based capsule, (2) thio-derivatized resorcin[4]arene analogs can be covalently linked through disulfides, and (3) the increased acidity of aromatic thio-substituent is not sufficient to replace HCl as cocatalyst for capsule catalyzed terpene cyclizations. © 2021 American Chemical Society Show more
Publication status
publishedExternal links
Journal / series
Organic LettersVolume
Pages / Article No.
Publisher
American Chemical SocietyOrganisational unit
09585 - Tiefenbacher, Konrad / Tiefenbacher, Konrad
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