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

May 2023 CpBIG.svg 250px 1,1′,1′′,1′′′,1′′′ ′-(Cyclopenta-1,3-diene-1,2,3,4,5-pentayl)pentakis(4-butylbenzene) Cp[BIG] 161296-28-2 correct CAS 103879544 correct FDA YZ6AHM38KB 102025217 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 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 55 66 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. 10.1002/1521-3765(20000915)6:18<3426::AID-CHEM3426>3.0.CO;2-B Palladium-Catalyzed Arylation of Cyclopentadienes Chemistry - A European Journal 6 18 3426–3433 2000 Dyker Gerald Heiermann Jörg Miura Masahiro Inoh Jun-Ichi Pivsa-Art Sommai Satoh Tetsuya Nomura Masakatsu 11039536 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. 10.1002/zaac.201000192 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 2010 Kuchenbecker Dennis Harder Sjoerd Jansen Georg https://hal.archives-ouvertes.fr/hal-00599874/file/PEER_stage2_10.1002%252Fzaac.201000192.pdf The perarylated metallocenes, such as samarium, sometimes exhibit unusual stability. This is likely to be explained by hydrogen bonds between the substituents. 10.1002/anie.200705001 18257006 Remarkable Stability of Metallocenes with Superbulky Ligands: Spontaneous Reduction of SmIII to SmII Angewandte Chemie International Edition 47 11 2121–2126 2008 Ruspic Christian Moss John R. Schürmann Markus Harder Sjoerd 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. 10.1039/b809872g 18728882 Superbulky metallocene complexes of the heavier alkaline-earth metals strontium and barium Dalton Transactions 35 4742–6 2008 Orzechowski Lars Piesik Dirk F.-J. Ruspic Christian Harder Sjoerd References Category:Cyclopentadienes Category:Aromatic hydrocarbons