Cyclopentadienyl allyl palladium is an

organopalladium compound Organopalladium chemistry is a branch of organometallic chemistry that deals with organic palladium compounds and their reactions. Palladium is often used as a catalyst in the reduction of alkenes and alkynes with hydrogen. This process involves the ...

with formula (C₅H₅)Pd(C₃H₅). This reddish solid is volatile with an unpleasant

odor An odor (American English) or odour (Commonwealth English; see spelling differences) is caused by one or more volatilized chemical compounds that are generally found in low concentrations that humans and animals can perceive via their sense ...

. It is soluble in common organic solvents. The molecule consists of a Pd centre sandwiched between a Cp and allyl ligands.

Preparation

This complex is produced by the reaction of

allylpalladium chloride dimer Allylpalladium(II) chloride dimer (APC) is a chemical compound with the chemical formula, formula hapticity, η3-C3H5)PdCl. This yellow air-stable compound is an important catalyst used in organic synthesis.Tatsuno, Y.; Yoshida, T.; Otsuka, S. ...

with

sodium cyclopentadienide Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp− is the cyclopentadienide anion. Sodium cyclopentadienide is a colorless solid, although samples often are p ...

: :2 C₅H₅Na + (C₃H₅)₂Pd₂Cl₂ → 2 (C₅H₄)Pd(C₃H₅) + 2 NaCl

Structure and reactions

The 18-electron complex adopts a half-sandwich structure with C_s symmetry, i.e., the molecule has a plane of symmetry. The complex can be decomposed readily by

reductive elimination Reductive elimination is an elementary step in organometallic chemistry in which the oxidation state of the metal center decreases while forming a new covalent bond between two ligands. It is the microscopic reverse of oxidative addition, and is ...

. :C₃H₅PdC₃H₅ → Pd(0) + C₅H₅C₃H₅ The compound readily reacts with alkyl

isocyanide An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragme ...

s to produce clusters with the approximate formula d(CNR)₂sub>n. It reacts with bulky alkyl

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

s to produce two-coordinated palladium(0) complexes: :CpPd(allyl) + 2 PR₃ → Pd(PR₃)₂ + C₅H₅C₃H₅ The compound has been used to deposit thin film

chemical vapor deposition Chemical vapor deposition (CVD) is a vacuum deposition method used to produce high quality, and high-performance, solid materials. The process is often used in the semiconductor industry to produce thin films. In typical CVD, the wafer (subst ...

of metallic

palladium Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself ...

References

{{Palladium compounds Cyclopentadienyl complexes Organopalladium compounds Allyl complexes