1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene

1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene
Names
Preferred IUPAC name
1,2,3,4,5-Pentakis(4-butylphenyl)cyclopenta-1,3-diene
Other names
Cp[BIG]
Identifiers
3D model (JSmol)
UNII
  • InChI=1S/C55H66/c1-6-11-16-41-21-31-46(32-22-41)51-52(47-33-23-42(24-34-47)17-12-7-2)54(49-37-27-44(28-38-49)19-14-9-4)55(50-39-29-45(30-40-50)20-15-10-5)53(51)48-35-25-43(26-36-48)18-13-8-3/h21-40,51H,6-20H2,1-5H3
    Key: CZMWDGMAEHAEDB-UHFFFAOYSA-N
  • CCCCC1=CC=C(C=C1)C2C(=C(C(=C2C3=CC=C(C=C3)CCCC)C4=CC=C(C=C4)CCCC)C5=CC=C(C=C5)CCCC)C6=CC=C(C=C6)CCCC
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).

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

  1. ^ 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.
  2. ^ Kuchenbecker, Dennis; Harder, Sjoerd; Jansen, Georg (2010). "Insight in Structures of Superbulky Metallocenes with the CpBIG Ligand: Theoretical Considerations of Decaphenyl Metallocenes" (PDF). Zeitschrift für Anorganische und Allgemeine Chemie. 636 (12): 2257–2261. doi:10.1002/zaac.201000192.
  3. ^ 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.
  4. ^ 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.