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). verify (what is ?) 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]

References

^ ^a ^b Y. Tatsuno, T. Yoshida, S. Otsuka (1979). Shriver, Duward F. (ed.). Inorganic Syntheses. Vol. 19. p. 220. doi:10.1002/9780470132500. ISBN 978-0-470-13250-0. {{cite book}}: |journal= ignored (help)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. (1989). "Selective area deposition of conducting palladium films on polyimide resins". Mater. Res. Soc. Symp. Proc. 158: 103–7. doi:10.1557/PROC-158-103. S2CID 97425013.
^ 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.

[Otsuka-1] Y. Tatsuno, T. Yoshida, S. Otsuka (1979). Shriver, Duward F. (ed.). Inorganic Syntheses. Vol. 19. p. 220. doi:10.1002/9780470132500. ISBN 978-0-470-13250-0. {{cite book}}: |journal= ignored (help)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. (1989). "Selective area deposition of conducting palladium films on polyimide resins". Mater. Res. Soc. Symp. Proc. 158: 103–7. doi:10.1557/PROC-158-103. S2CID 97425013.

[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.

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