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EnglishC3-Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis) avoiding the use of noxious, expensive and limited market availability reagents, with complete recovery of the undesired Cs co-product that is quantitatively recovered and converted back into HHTP. The C3-symmetric triphenylene product was further functionalized through substitution, deprotection and Mannich condensation reactions affording a series of C3-symmetric functionalized scaffolds in good yields for supramolecular applications.
| Titolo: | Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives |
| Autori: | SCARSO, ALESSANDRO (Corresponding) |
| Data di pubblicazione: | 2018 |
| Data ahead of print: | 28-giu-2018 |
| Stato di pubblicazione: | Pubblicato |
| Rivista: | |
| Abstract: | C3-Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis) avoiding the use of noxious, expensive and limited market availability reagents, with complete recovery of the undesired Cs co-product that is quantitatively recovered and converted back into HHTP. The C3-symmetric triphenylene product was further functionalized through substitution, deprotection and Mannich condensation reactions affording a series of C3-symmetric functionalized scaffolds in good yields for supramolecular applications. |
| Handle: | http://hdl.handle.net/11368/2961480 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1039/c8qo00414e |
| URL: | https://pubs.rsc.org/en/content/articlelanding/2018/QO/C8QO00414E#!divAbstract |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| Org. Chem. Front. 2018, Definitivo.pdf | Documento in Versione Editoriale | Copyright Editore | Administrator Richiedi una copia |
Utilizza questo identificativo per citare o creare un link a questo documento:
http://hdl.handle.net/11368/2961480
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