Chemistry:1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene
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| Names | |
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| Preferred IUPAC name
1,2,3,4,5-Pentakis(4-butylphenyl)cyclopenta-1,3-diene | |
| Other names
Cp[BIG]
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C55H66 | |
| Molar mass | 727.133 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene is an organochemical compound from the diene group and a cyclopentadiene derivative. The anion of this compound is used as a sterically demanding ligand, often abbreviated as Cp[BIG], in the organometallic chemistry of sandwich compounds.
Preparation
1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene can be prepared in a one-step reaction by the palladium-catalyzed reaction of Zirconocene dichloride with 4-n-butylbenzene bromide.[1]
Reactions
1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene reacts directly with a range of organometallic compounds or in reduced form as a sodium or potassium compound with the salts of main-group and transition metals. The resulting metallocenes, in contrast to the unsubstituted Pentaphenylcyclopentadienyl complexes are in various solvents readily soluble.[2] The perarylated metallocenes, such as samarium, sometimes exhibit unusual stability. This is likely to be explained by hydrogen bonds between the substituents.[3] The reaction of 1,2,3,4,5-pentakis(4-butylphenyl)-1,3-cyclopentadiene with strong basic strontium and barium compounds provides the corresponding coplanar sandwich compounds.[4]
References
- ↑ Dyker, Gerald; Heiermann, Jörg; Miura, Masahiro; Inoh, Jun-Ichi; Pivsa-Art, Sommai; Satoh, Tetsuya; Nomura, Masakatsu (2000). "Palladium-Catalyzed Arylation of Cyclopentadienes". Chemistry - A European Journal 6 (18): 3426–3433. doi:10.1002/1521-3765(20000915)6:18<3426::AID-CHEM3426>3.0.CO;2-B. PMID 11039536.
- ↑ Kuchenbecker, Dennis; Harder, Sjoerd; Jansen, Georg (2010). "Insight in Structures of Superbulky Metallocenes with the CpBIG Ligand: Theoretical Considerations of Decaphenyl Metallocenes". Zeitschrift für Anorganische und Allgemeine Chemie 636 (12): 2257–2261. doi:10.1002/zaac.201000192. https://hal.archives-ouvertes.fr/hal-00599874/file/PEER_stage2_10.1002%252Fzaac.201000192.pdf.
- ↑ Ruspic, Christian; Moss, John R.; Schürmann, Markus; Harder, Sjoerd (2008). "Remarkable Stability of Metallocenes with Superbulky Ligands: Spontaneous Reduction of SmIII to SmII". Angewandte Chemie International Edition 47 (11): 2121–2126. doi:10.1002/anie.200705001. PMID 18257006.
- ↑ Orzechowski, Lars; Piesik, Dirk F.-J.; Ruspic, Christian; Harder, Sjoerd (2008). "Superbulky metallocene complexes of the heavier alkaline-earth metals strontium and barium". Dalton Transactions (35): 4742–6. doi:10.1039/b809872g. PMID 18728882.
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