Mister Pommeroy:
[[File:CpBIG.svg|thumb|1,2,3,4,5-Pentakis(4-butylphenyl)-1,3-cyclopentadiene]]
'''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<sup>[BIG]</sup>, in the organometallic chemistry of [[sandwich compound]]s.
== 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.<ref name="Dyker">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, p. 3426–3433, .</ref>
== 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 metal]]s. The resulting metallocenes, in contrast to the unsubstituted Pentaphenylcyclopentadienyl complexes are in various solvents readily soluble.<ref name="Harder3">Dennis Kuchenbecker, [[Sjoerd Harder]], Georg Jansen: ''Insight in Structures of Superbulky Metallocenes with the Cp<sup>[BIG]</sup> Ligand: Theoretical Considerations of Decaphenyl-Metallocenes.'' In: ''[[Zeitschrift für anorganische und allgemeine Chemie]].'' 636, 2010, p. 2257–2261, [[doi:10.1002/zaac.201000192]].</ref> The perarylated metallocenes, such as [[Samarium]], sometimes exhibit unusual stability. This is likely to be explained by hydrogen bonds between the substituents.<ref name="Harder4">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, p. 2121–2126, [[doi:10.1002/anie.200705001]].</ref> 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.<ref name="Harder2">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, p. 4742–4746, [[doi:10.1039/b809872g]].</ref>
== References ==
<references />
[[Category:Cyclopentadienes]]
[[Category:Aromatic hydrocarbons]]
'''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<sup>[BIG]</sup>, in the organometallic chemistry of [[sandwich compound]]s.
== 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.<ref name="Dyker">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, p. 3426–3433, .</ref>
== 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 metal]]s. The resulting metallocenes, in contrast to the unsubstituted Pentaphenylcyclopentadienyl complexes are in various solvents readily soluble.<ref name="Harder3">Dennis Kuchenbecker, [[Sjoerd Harder]], Georg Jansen: ''Insight in Structures of Superbulky Metallocenes with the Cp<sup>[BIG]</sup> Ligand: Theoretical Considerations of Decaphenyl-Metallocenes.'' In: ''[[Zeitschrift für anorganische und allgemeine Chemie]].'' 636, 2010, p. 2257–2261, [[doi:10.1002/zaac.201000192]].</ref> The perarylated metallocenes, such as [[Samarium]], sometimes exhibit unusual stability. This is likely to be explained by hydrogen bonds between the substituents.<ref name="Harder4">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, p. 2121–2126, [[doi:10.1002/anie.200705001]].</ref> 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.<ref name="Harder2">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, p. 4742–4746, [[doi:10.1039/b809872g]].</ref>
== References ==
<references />
[[Category:Cyclopentadienes]]
[[Category:Aromatic hydrocarbons]]
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