Loading...
Please wait, while we are loading the content...
Similar Documents
Racemic and Meso Crystal Structures of an Axial-Chiral Spirobi-(dinaphthoazepin)ium Salt: Emergence of an $S_{4}$-Symmetric Molecule
| Content Provider | MDPI |
|---|---|
| Author | Honegger, Philipp Gajic, Natalie Prado-Roller, Alexander Widhalm, Michael |
| Copyright Year | 2021 |
| Description | To date, only a few instances of $S_{4}$-symmetric organic molecules exist. In principle, spirobi-(dinaphthoazepin)ium cations can achieve this highly symmetric point group. Heating racemic 2,2′-bis(bromomethyl)-1,1′binaphthyl with aqueous ammonia afforded a mixture of rac- and meso-3,3′,5,5′-tetrahydro-4,4′-spirobi[dinaphtho[2,1-c:1′,2′-e]azepin]-4-ium bromide which was separated by fractional crystallisation. Both stereoisomers were characterised spectroscopically, and their crystal structures were determined and compared. The rac crystal structure differs significantly from the known enantiopure one. The meso molecules display a near-perfect $S_{4}$ symmetry. Upon treatment with $KO^{t}$Bu, both isomers undergo Stevens rearrangement. |
| Starting Page | 1365 |
| e-ISSN | 20738994 |
| DOI | 10.3390/sym13081365 |
| Journal | Symmetry |
| Issue Number | 8 |
| Volume Number | 13 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-07-27 |
| Access Restriction | Open |
| Subject Keyword | Symmetry Crystal Structure Three-dimensional Structure Chirality Axial Chirality Racemate Meso Spiro Compound Stevens Rearrangement |
| Content Type | Text |
| Resource Type | Article |
