Synthesis and Application of [2.2]Paracyclophane Derivatives in Catalysis and Material Science
Christoph Zippel
Diese Publikation zitieren
Christoph Zippel, Synthesis and Application of [2.2]Paracyclophane Derivatives in Catalysis and Material Science (2021), Logos Verlag, Berlin, ISBN: 9783832585099
Beschreibung / Abstract
[2.2]Paracyclophane is a prevalent Ïâstacked, carbocyclic scaffold with a âbent and batteredâ structure. This results not only in a transannular communication but also in a chiral plane within the molecule if at least one substituent is present. These unique properties make this structure synthetically challenging but also scarcely investigated.
A new method for enantio-separation based on kinetic resolution was developed, which allows the access to enantiomerically pure [2.2]paracyclophane-based building blocks. In a liquid crystal templated chemical vapor deposition process, [2.2]paracyclophanyl alcohols containing an additional central chiral element were evaluated for the self-assembly of nanofibers. Furthermore, the cyclopropanation of α-alkyl-α-diazo compounds with a [2.2]paracyclophane-based rhodium tetracarboxylate complex was investigated. Finally, the rigidity, regioselective functionalization, and transannular communication of [2.2]paracyclophane were exploited in the design of heterobimetallic Au(I)/Ru(II) complexes for the study of metal-to-metal interactions.
A new method for enantio-separation based on kinetic resolution was developed, which allows the access to enantiomerically pure [2.2]paracyclophane-based building blocks. In a liquid crystal templated chemical vapor deposition process, [2.2]paracyclophanyl alcohols containing an additional central chiral element were evaluated for the self-assembly of nanofibers. Furthermore, the cyclopropanation of α-alkyl-α-diazo compounds with a [2.2]paracyclophane-based rhodium tetracarboxylate complex was investigated. Finally, the rigidity, regioselective functionalization, and transannular communication of [2.2]paracyclophane were exploited in the design of heterobimetallic Au(I)/Ru(II) complexes for the study of metal-to-metal interactions.
Inhaltsverzeichnis
- BEGINN
- 1 INTRODUCTION
- 1.1 [2.2]CYCLOPHANES
- 1.2 PHOTOREDOX CATALYSIS
- 2 OBJECTIVE
- 3 MAIN SECTION
- 3.1 KINETIC RESOLUTION/DESYMMETRIZATION OF ACETYL[2.2]PARACYCLOPHANES
- 3.2 PHOTO-ARBUZOV REACTION
- 3.3 CHIRAL NANOFIBERS BY CHEMICAL VAPOR DEPOSITION POLYMERIZATION
- 3.4 ASYMMETRIC CYCLOPROPANATION WITH RHODIUM PADDLEWHEEL COMPLEXES
- 3.5 COOPERATIVE AU(I)/RU(II) PHOTOREDOX CATALYSIS
- 4 SUMMARY AND OUTLOOK
- 4.1 KINETIC RESOLUTION/DESYMMETRIZATION OF ACETYL[2.2]PARACYCLOPHANES
- 4.2 PHOTO-ARBUZOV REACTION
- 4.3 CHIRAL NANOFIBERS BY CHEMICAL VAPOR DEPOSITION POLYMERIZATION
- 4.4 ASYMMETRIC CYCLOPROPANATION WITH RHODIUM PADDLEWHEEL COMPLEXES
- 4.5 COOPERATIVE AU(I)/RU(II) PHOTOREDOX CATALYSIS
- 5 EXPERIMENTAL SECTION
- 5.1 GENERAL REMARKS
- 5.2 KINETIC RESOLUTION/DESYMMETRIZATION OF ACETYL[2.2]PARACYCLOPHANES
- 5.3 PHOTO-ARBUZOV REACTION
- 5.4 CHIRAL NANOFIBERS BY CHEMICAL VAPOR DEPOSITION
- 5.5 RHODIUM PADDLEWHEEL COMPLEXES
- 5.6 COOPERATIVE AU(I)/RU(II) PHOTOREDOX CATALYSIS
- 5.7 CRYSTALLOGRAPHIC DATA
- 6 LIST OF ABBREVIATIONS
- 7 BIBLIOGRAPHY
- 8 APPENDIX
- 8.1 CURRICULUM VITAE
- 8.2 LIST OF PUBLICATIONS
- 8.3 ACKNOWLEDGMENTS