Oxidation of tetramethylthiuram sulfide and iron(III) dithiocarbamates with ferric chloride

Victoriano, Luis I.; Gnecco, Juan A.; Carbacho, Hernán V.

doi:10.1016/0277-5387(95)00380-0

Cited by 9 publications

(11 citation statements)

References 25 publications

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“…Reactions (1) and ( 2) are the same as the results reported by Victoriano et al, 9 whilst in the step (3), bis(dialkylimonium)tetrathiolane (bitt-4) is possibly formed instead of bis(dialkylimonium)trithiolane (bitt-3) 9 in the presence of the monomer MMA and PPh 3 . Bitt-4 may discompose into (diethylthiocarbamoyl)sulfur chloride (Et 2 NCS 2 Cl) as shown in step (4).…”

supporting

confidence: 76%

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A novel ATRP initiating system Fe(dtc)3/FeCl3/PPh3 for MMA polymerization

Chen

Qiu

2000

Chem. Commun.

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supporting

confidence: 76%

“…According to the above results and the reaction of Fe(dtc) 3 with FeCl 3 reported in the literature 9 and our previous work, 6 we propose the reaction of Fe(dtc) 3 with FeCl 3 as shown in Scheme 1.…”

supporting

confidence: 73%

A novel ATRP initiating system Fe(dtc)3/FeCl3/PPh3 for MMA polymerization

Chen

Qiu

2000

Chem. Commun.

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“…No special precautions to exclude water and/or air were taken. This was an important modification to previous experimental procedures, 20 which made extensive use of Schlenk or cannulation techniques. 21 CuBr2 was prepared from CuBr and an excess of Br 2.…”

Section: Methodsmentioning

confidence: 99%

“…Thus, tetramethylthiuram monosulfide and FeCl 3 afford 3,5-bis(N,N-dimethyliminio)-1,2,4trithiolane pentachloroferrate(III). 20 The studies of this unusual pattern of reactivity are now extended to the reaction of thiuram monosulfides and copper(II) halides.…”

Section: Introductionmentioning

confidence: 99%

Reaction of Bis(N,N-dimethylthiocarbamoyl) Sulfide with Copper(II) Halides and the Crystal and Molecular Structures of Halogeno(bis(N,N-dimethylthiocarbamoyl) sulfido)copper(I) Complexes

1997

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Bis(N,N-dimethylthiocarbamoyl) sulfide (Tetramethylthiuram monosulfide) reacts with copper(II) halides ( halide) Cl and Br) to yield 3,5-bis(N,N-dialkyliminio)-1,2,4-trithiolane trihalocuprate(I) and the neutral halogeno(bis-(N,N-dimethylthiocarbamoyl) sulfido)copper(I) complex. The proposed structure for the trihalocuprate(I) compounds is supported mostly by infrared studies. The copper(I) adducts may also be prepared by straightforward reaction of copper(I) halides and the ligand, and single-crystal x-ray studies show a wide diversity of structural variations. All molecules consist of basic S 2 CuX units. The Cl derivative (1) is an S-bridged dimer (C 6 H 14 -ClCuN 2 OS 3 , monoclinic, P2 1 /c (No. 14), Z ) 4, a ) 9.525(8) Å, b ) 13.022(10) Å, c ) 10.835(7) Å), while the Br analogue (2) features a polymeric network of S 2 CuBr units, also bridged by S atoms (C 6 H 12 BrCuN 2 S 3 , orthorhombic, P2 1 2 1 2 1 (No.19), Z ) 4, a ) 7.043(2) Å, b ) 9.442(3) Å, c ) 17.889(4) Å). The iodo compound (3) exists as a halogen-bridged dimer (C 6 H 12 CuIN 2 S 3, monoclinic, P2 1 /m (No. 11), Z ) 4, a ) 9.570(1) Å, b ) 10.578(1) Å, c ) 12.422(1) Å). The molecular structures found support the assignment of the IR and Raman spectral data in all three cases. The diversity of structural variations is attributed to the relative basicity of the S and halogen potential bridging atoms. Molecular weight studies in acetonitrile are consistent with a monomer for 2, while the temperature dependence of the 1 H-NMR for 1 is interpreted in terms of a monomer-dimer equilibrium.

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“…The ligand may also undergo a two-electron oxidation to the cyclic organic dication of 1,2,4-trithiolane-3,5-diimine, which has been isolated as a metal-halogen anionic complex. 5, 14 In a recent publication 5 we reported the crystal and molecular structures of [bis(dimethylthiocarbamoyl) sulfide]halogenocopper() complexes [CuL Me (X)] [X = Cl, Br or I; L Me = Me 2 NC(S)SC(S)NMe 2 ]. In all three structural studies it was found that the basic XCuS 2 units undergo more extensive association to afford dimers (X = Cl or I) or a polymer (X = Br).…”

mentioning

confidence: 99%