DISTAL dibromoresorcin[4]arenes through selective deactivation
- A simple and straightforward regioselective synthesis of distal disubstituted resorcin[4]arenes was developed, avoiding competing substitution patterns at an early stage via regioselective deactivation. Product limiting reaction steps were optimized by starting material recovery and by an improved protocol for ester cleavage while providing simple workup procedures throughout the synthesis without requiring column chromatography. The cyclizing acetalization of distal disubstituted resorcinarene octols proved to be a high yield process without oligomer formation, although less sterically controlled compared to the usual tetrabromo case.
| Author: | Dominic Sebastian DanielsiekORCiDGND, Gerald DykerORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-99339 |
| DOI: | https://doi.org/10.1002/ejoc.202001031 |
| Parent Title (English): | European journal of organic chemistry |
| Subtitle (English): | a practical optimization |
| Publisher: | Wiley-VCH |
| Place of publication: | Hoboken, New Jersey |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2023/06/01 |
| Date of first Publication: | 2020/11/04 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Tag: | Macrocycles; Molecular bowls; Regioselective deactivation; Resorcinarenes; Selective difunctionalization; Supramolecular chemistry |
| Volume: | 2020 |
| Issue: | 42 |
| First Page: | 6570 |
| Last Page: | 6575 |
| Note: | Dieser Beitrag ist auf Grund des DEAL-Wiley-Vertrages frei zugänglich. |
| Institutes/Facilities: | Lehrstuhl für Organische Chemie II |
| Dewey Decimal Classification: | Naturwissenschaften und Mathematik / Chemie, Kristallographie, Mineralogie |
| open_access (DINI-Set): | open_access |
| faculties: | Fakultät für Chemie und Biochemie |
| Licence (English): |  Creative Commons - CC BY-NC-ND 4.0 - Attribution-NonCommercial-NoDerivatives 4.0 International |
