581106-71-0

Basic information

• Product Name: [Pd(PPh₃)₂(η¹-SCNMe₂)(Cl)]
• CAS NO: 581106-71-0
• Molecular Weight: 754.608
• Mol File: 581106-71-0.mol

Chemical Properties

• CAS DataBase Reference: [Pd(PPh₃)₂(η¹-SCNMe₂)(Cl)](CAS DataBase Reference)
• NIST Chemistry Reference: [Pd(PPh₃)₂(η¹-SCNMe₂)(Cl)](581106-71-0)
• EPA Substance Registry System: [Pd(PPh₃)₂(η¹-SCNMe₂)(Cl)](581106-71-0)

Safety Data

• Hazardous Substances Data: 581106-71-0(Hazardous Substances Data)

Upstream product

• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 581106-71-0 [Pd(PPh₃)₂(η¹-SCNMe₂)(Cl)] 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 

Downstream Products

• 79969-97-4 [Pd(PPh₃)Cl]₂(μ,η²-SCNMe₂)₂ 
• 650634-64-3 [Pd(PPh₃){η¹-C(SEt)(NMe₂)}(η²-S₂CO)] 
• 650634-65-4 [Pd(PPh₃)₂(η¹-SCNMe₂)(η²-S₂COEt)] 
• 581782-50-5 [Pd(PPh₃)Cl]₂(μ,η²-SCNMe₂)_2*CH2Cl2 
• 581106-74-3 [Pd(triphenylphosphine)2(η2-SCNMe2)]PF6 

Relevant articles and documents

Synthesis, dissociation behavior and crystal structures of palladium(II) complexes with N,N-dimethylthiocarbamoyl, Me2NC=S, containing ligand: Structures of [Pd(PPh3)2(η1-SCNMe2)(Cl)], [Pd(PPh3)(Cl)]2(μ,η2-SCNMe2)2, [Pd(PPh3)2{η1-C(SMe)(NMe2)}(η2-S2CO)], and [Pd{η1-SC(O)NMe2}Pd(Cl)](μ,η2-SCNMe2)(μ,η2-dppm)2

Treatment of Pd(PPh3)4 with N,N-dimethylthiocarbamoyl chloride, Me2NC(=S)Cl, in dichloromethane at -20 °C produces complex [Pd(PPh3)2(η1-SCNMe2)(Cl)] (1). In solution state, complex 1 shows the intramolecular dissociation of the chloride or intermolecular dissociation of the triphenylphosphine ligands to form η2-thiocarbamoyl complex [Pd(PPh3)2(η2-SCNMe2)][Cl] (2) or the bridging η2-thiocarbamoyl dipalladium complex [Pd(PPh3)Cl]2(μ,η2-SCNMe2)2 (3). Treatment of 1 with MeOCS2K yields [Pd(PPh3){η1-C(SMe)(NMe2)}(η2-S2CO)] (5a). The Fischer-type carbene-complex 5a is formed via methyl migration of the methyldithiocarbonate to thiocarbamoyl ligand. Complex 1 reacts with EtOCS2K resulting in the formation of η2-dithiocarbonate complex [Pd(PPh3)(η1-SCNMe2)(η2-S2COEt)] (4b) and carbene-complex [Pd(PPh3){η1-C(SEt)(NMe2)}(η2-S2CO)] (5b) with ratios of 10:1 from the integration of 31P{1H} NMR spectra. By continuously stirring the mixtures 4b and 5b in CH2Cl2 solution for 2 h, complex 5b was formed as the final product. Complex [Pd(η1-SCNMe2)(η2-Phen)(Cl)] (6) or [Pd{η1-SC(O)NMe2}Pd(Cl)](μ,η2-SCNMe2)- (μ,η2-dppm)2 (7) is accessible by the reaction of 1 with phen (1,10-phenanthroline) or dppm {bis(diphenylphosphino) methane} in dichloromethane at room temperature. All of the complexes are identified by spectroscopic methods and complexes 1, 3, 5a, and 7 are determined by single-crystal X-ray diffraction. The complexes 1 and 3 crystallize in the monoclinic space group P21/n and P21/c with Z = 4, respectively, whereas 5a and 7 belong to the triclinic space group P1 with Z = 2. The cell dimensions are as follows: for 1, a = 12.8248(1) ?, b = 18.6358(2) ?, c = 14.9692(1) ?, β = 105.1513(4)°; for 3, a = 9.8782(1) ?, b = 11.7238(1) ?, c = 20.7353(2) ?, α = 103.9126(5)°, β = 97.8453(3)°, γ = 104.9669(5)°; for 5a, a = 16.3638(2) ?, b = 9.3374(1) ?, c = 15.7117(2) ?, β = 98.2957(6)°; for 7, a = 12.1128(1) ?, b = 14.0133(2) ?, c = 17.7873(2) ?, α = 82.1939(5), β = 79.6190(6)°, γ = 80.9551(5)°.

Sulfur-assisted chloride and triphenylphosphine dissociation of palladium(II) complex. See abstract

Treatment of Pd(PPh3)4 with Me2NC(=S)Cl in dichloromethane at -20 °C produces the complex [Pd(PPh3)2(η1-SCNMe2) (Cl)], 2. Variable temperature 1H and 31P{H}