Cyclopentadienyl allyl palladium

Cyclopentadienyl allyl palladium
Names
	Other names (Cp)Pd(allyl)
Identifiers
CAS Number	1271-03-0 ;
ChemSpider	11466724;
PubChem CID	57347372 PubChem has erroneous structure;
Properties
Chemical formula	C8H10Pd
Molar mass	212.59 g·mol−1
Appearance	Reddish needle-shaped solid
Melting point	60 to 62 °C (140 to 144 °F; 333 to 335 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Cyclopentadienyl allyl palladium is an organopalladium compound with formula (C₅H₅)Pd(C₃H₅). This reddish solid is volatile with an unpleasant odor. It is soluble in common organic solvents. The molecule consists of a Pd centre sandwiched between a Cp and allyl ligands.[1]

Preparation

This complex is produced by the reaction of allylpalladium chloride dimer with sodium cyclopentadienide:[1][2]

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.

C₃H₅PdC₃H₅ → Pd(0) + C₅H₅C₃H₅

The compound readily reacts with alkyl isocyanides to produce clusters with the approximate formula [Pd(CNR)₂]_n. It reacts with bulky alkyl phosphines to produce two-coordinated palladium(0) complexes:[3]

CpPd(allyl) + 2 PR₃ → Pd(PR₃)₂ + C₅H₅C₃H₅

The compound has been used to deposit thin film chemical vapor deposition of metallic palladium.[4][5]

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References

Y. Tatsuno, T. Yoshida, S. Otsuka (1979). Shriver, Duward F. (ed.). "(3-Allyl)Palladium(II) Complexes". Inorg. Synth. Inorganic Syntheses. 19: 220. doi:10.1002/9780470132500. ISBN 978-0-470-13250-0.CS1 maint: multiple names: authors list (link)
R. B. King (1963). "Organometallic Chemistry of the Transition Metals. Organometallic Chemistry of the Transition Metals. III. Reactions between Sodium Cyclopentadienide and Certain Complex Transition Metal Halides". Inorg. Chem. 2 (3): 528. doi:10.1021/ic50007a026.
Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. (1976). "Cyclohexyneplatinum(0) Complexes Containing Di-t-butylphenylphosphine, t-butyldiphenylphosphine or Trimethylphosphine". Australian Journal of Chemistry. 45 (1): 135–142. doi:10.1071/CH9920135.
Y. G Kim; S. Bialy; R.W. Miller; J. T. Spencer; Dowben A. Peter; Datta S. "Selective area deposition of conducting palladium films on polyimide resins". Ma. Res. Soc. Symp. Proc. 158: 103–7.
K. Rajalingam; T. Strunskus; A. Terfort; R. A. Fischer; C. Wo (2008). "Metallization of a thiol-terminated organic surface using chemical vapor deposition". Langmuir. 24 (15): 7886–7994. doi:10.1021/la8008927. PMID 18590295.

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[Otsuka-1] Y. Tatsuno, T. Yoshida, S. Otsuka (1979). Shriver, Duward F. (ed.). "(3-Allyl)Palladium(II) Complexes". Inorg. Synth. Inorganic Syntheses. 19: 220. doi:10.1002/9780470132500. ISBN 978-0-470-13250-0.CS1 maint: multiple names: authors list (link)

[2] R. B. King (1963). "Organometallic Chemistry of the Transition Metals. Organometallic Chemistry of the Transition Metals. III. Reactions between Sodium Cyclopentadienide and Certain Complex Transition Metal Halides". Inorg. Chem. 2 (3): 528. doi:10.1021/ic50007a026.

[3] Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. (1976). "Cyclohexyneplatinum(0) Complexes Containing Di-t-butylphenylphosphine, t-butyldiphenylphosphine or Trimethylphosphine". Australian Journal of Chemistry. 45 (1): 135–142. doi:10.1071/CH9920135.

[4] Y. G Kim; S. Bialy; R.W. Miller; J. T. Spencer; Dowben A. Peter; Datta S. "Selective area deposition of conducting palladium films on polyimide resins". Ma. Res. Soc. Symp. Proc. 158: 103–7.

[5] K. Rajalingam; T. Strunskus; A. Terfort; R. A. Fischer; C. Wo (2008). "Metallization of a thiol-terminated organic surface using chemical vapor deposition". Langmuir. 24 (15): 7886–7994. doi:10.1021/la8008927. PMID 18590295.