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- Title
Gram‐Scale Synthesis of the 1,1,n,n‐Tetramethyl[n](2,11)teropyrenophanes.
- Authors
Unikela, Kiran Sagar; Ghasemabadi, Parisa Ghods; Houska, Václav; Dawe, Louise N.; Zhao, Yuming; Bodwell, Graham J.
- Abstract
A gram‐scale synthesis of a series of 1,1,n,n‐tetramethyl[n](2,11)teropyrenophanes (n=7–9) has been accomplished as well as the first synthesis of the next higher homologue 1,1,10,10‐tetramethyl[10](2,11)teropyrenophane. The scale‐up of the original small‐scale synthesis required the development of several heavily modified synthetic methods, including a chlorination/Friedel–Crafts alkylation protocol and an iodination/Wurtz coupling protocol, which were performed on 25–30 g and 30–60 g scales, respectively. Two separate sets of conditions for the key teropyrene‐forming cyclodehydrogenation reaction at the end of the synthetic pathway were developed, an acid‐promoted one for the two less strained congeners and an acid‐free method for the two more strained homologues.
- Subjects
ALKYLATION; IODINATION; AROMATIC compounds; CATALYTIC dehydrogenation; PYRENE; WATER chlorination
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 1, p390
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202003828