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

from Wikipedia, the free encyclopedia
Structural formula
Structure of CpBIG
General
Surname 1,2,3,4,5-pentakis (4-butylphenyl) -1,3-cyclopentadiene
other names
  • 1,2,3,4,5-penta (4-butylphenyl) cyclopentadiene
  • Cp BIG
  • 1,1 ', 1' ', 1' '', 1 '' '' - (cyclopenta-1,3-diene-1,2,3,4,5-pentayl) pentakis (4-butylbenzene)
Molecular formula C 55 H 66
External identifiers / databases
CAS number 161296-28-2
PubChem 102025217
Wikidata Q63478273
properties
Molar mass 726.52 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2,3,4,5-pentakis (4-butylphenyl) -1,3-cyclopentadiene is an organic- chemical compound from the group of substances of dienes 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.

presentation

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.

Reactions

1,2,3,4,5-Pentakis (4-butylphenyl) -1,3-cyclopentadiene reacts directly with a number of organometallic compounds or in reduced form as sodium or potassium compounds with the salts of main and transition metals . In contrast to the unsubstituted pentaphenylcyclopentadienyl complexes, the resulting metallocenes are readily soluble in various solvents. Some of the perarylated metallocenes, for example from Samarium , have an unusual stability. This can probably be explained by hydrogen bonds between the substituents. 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.

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Gerald Dyker, Jörg Heiermann, Masahiro Miura, Jun-Ichi Inoh, Sommai Pivsa-Art, Tetsuya Satoh, Masakatsu Nomura: Palladium-Catalyzed Arylation of Cyclopentadienes. In: Chemistry - A European Journal . 6, 2000, pp. 3426-3433, doi : 10.1002 / 1521-3765 (20000915) 6:18 <3426 :: AID-CHEM3426> 3.0.CO; 2-B .
  3. ↑ Dennis Kuchenbecker, Sjoerd Harder , Georg Jansen: Insight in Structures of Superbulky Metallocenes with the Cp [BIG] Ligand: Theoretical Considerations of Decaphenyl-Metallocenes. In: Journal of Inorganic and General Chemistry . 636, 2010, pp. 2257-2261, doi: 10.1002 / zaac.201000192 .
  4. ↑ Christian Ruspic, John R. Moss, Markus Schürmann, Sjoerd Harder: Remarkable Stability of Metallocenes with SuperBulky Ligands: Spontaneous Reduction of SmIII to SmII. In: Angewandte Chemie International Edition . 47, 2008, pp. 2121-2126, doi: 10.1002 / anie.200705001 .
  5. ^ Lars Orzechowski, Dirk F.-J. Piesik, Christian Ruspic, Sjoerd Harder: Superbulky metallocene complexes of the heavier alkaline-earth metals strontium and barium. In: Dalton Transactions . 2008, pp. 4742-4746, doi: 10.1039 / b809872g .