Synthese und Eigenschaften von Diethyldithiocarbaminsäureperfluororganylestern, (C2H5)2NC(S)SRf (Rf = CF3, C2F5, i-C3F7, n-C4F9, C6F5)

Wessel, Werner; Tyrra, Wieland; Naumann, Dieter

doi:10.1002/1521-3749(200106)627:6<1264::aid-zaac1264>3.0.co;2-j

Cited by 10 publications

(3 citation statements)

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“…99,100 Trifluoromethyl silver has also been used in the synthesis of trifluoromethyl derivatives of various elements of the groups 12-16, 100,102 and in the trifluoromethylation of organic substrates. [34][35][36]38,39,103 A few Au(III) trifluoromethyl complexes have been prepared by transmetallation reactions between Cd(CF 3 ) 2 •DME or Me 3 SiCF 3 and Au(III) precursors, 61,88,98 although mixtures of Au(I) and Au(III) complexes frequently result from these reactions (see below). 61,88 Oxidative addition of ICF 3…”

Section: Overview Of the Synthetic Methods Used For The Formation Of ...mentioning

confidence: 99%

“…100,101 The NMR studies carried out by the same authors showed that these solutions contain equilibrium mixtures of [Ag(CF 3 )(solvent)] and [Ag(solvent) 2 ][Ag(CF 3 ) 2 ]. [34][35][36]38,39,103 A few Au(III) trifluoromethyl complexes have been prepared by transmetallation reactions between Cd(CF 3 ) 2 ·DME or Me 3 SiCF 3 and Au(III) precursors, 61,88,98 although mixtures of Au(I) and Au(III) complexes frequently result from these reactions (see below). [34][35][36]38,39,103 A few Au(III) trifluoromethyl complexes have been prepared by transmetallation reactions between Cd(CF 3 ) 2 ·DME or Me 3 SiCF 3 and Au(III) precursors, 61,88,98 although mixtures of Au(I) and Au(III) complexes frequently result from these reactions (see below).…”

Section: Transmetallationmentioning

confidence: 99%

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Gold trifluoromethyl complexes

Gil‐Rubio

Vicente

2015

Dalton Trans.

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This article reviews the synthesis, reactivity and applications of gold trifluoromethyl complexes, which are the only isolated perfluoroalkyl complexes of gold. The most reported examples are neutral Au(i) complexes of the type [Au(CF3)L], whereas only two Au(ii) trifluoromethyl complexes have been reported, both being diamagnetic and containing a strong Au-Au bond. A number of Au(iii) trifluoromethyl complexes have been prepared by oxidative addition of halogens or iodotrifluoromethane to Au(i) complexes or, in a few cases, by transmetallation reactions. Owing to the limitations of the available synthetic methods, a lower number of examples is known, particularly for the oxidation states (ii) and (iii). Gold trifluoromethyl complexes present singular characteristics, such as thermal stability, strong Au-C bonds and, in some cases, reactive α-C-F bonds. Some of the Au(iii) complexes reported, show unusually easy reductive elimination reactions of trifluoromethylated products which could be applied in the development of gold-catalyzed processes for the trifluoromethylation of organic compounds.

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Section: Overview Of the Synthetic Methods Used For The Formation Of ...mentioning

confidence: 99%

Section: Transmetallationmentioning

confidence: 99%

Gold trifluoromethyl complexes

Gil‐Rubio

Vicente

2015

Dalton Trans.

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“…Although reports exist on the synthesis of fluorinated dithiocarbamates [ 33 – 35 ], the direct trifluoromethylation of dithiocarbamates has not been described. In 2001 Naumann and co-workers [ 36 ] have published a reaction of tetraethylthiuram disulfide with perfluoroorganosilver and perfluoroorganocadmium reagents proceeding most probably by a radical mechanism ( Scheme 1 ). This method suffers from several drawbacks such as extra reaction steps for the preparation of the thiuram disulfide and the use of expensive and environmentally problematic heavy metals.…”

Section: Introductionmentioning

confidence: 99%

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

Halimehjani

Dračínský

Beier

2017

Beilstein J. Org. Chem.

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A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni’s reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C–N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.

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Syntheses, Characterizations, and Crystal Structures of β‐Diketiminato Compounds of Pentafluorophenyl Group 12 Derivatives, HC{[C(Me)N(C₆H₃‐2, 6‐i‐Pr₂)]₂}MC₆F₅ (M = Zn, Cd)

Aboulkacem

Tyrra

Pantenburg

2003

Zeitschrift anorg allge chemie

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The reactions of H2C[C(Me)N(C6H3‐2, 6‐i‐Pr2)]2 ((DPP)2NacNacH) and Zn(C6F5)2 · 2 EtCN or Cd(C6F5)2 · 2 MeCN in a molar ratio of approximately 1:1 selectively gave the derivatives (DPP)2NacNacMC6F5 (M = Zn, Cd) in excellent yields. No reaction was observed between (DPP)2NacNacH and Hg(C6F5)2 under similar conditions. Reactions with Hg(C6F5)OCOMe yielded the products of dismutation, Hg(C6F5)2 and Hg(OCOMe)2. (DPP)2NacNacZnC6F5 crystallises as a 1:1 adduct with THF with two independent molecules per unit cell (triclinic, P1 (no. 2)). The zinc atom is tetrahedrally surrounded by the chelating ligand, the pentafluorophenyl group and one THF molecule. A similar situation is found in the 1:1 adduct of (DPP)2NacNacCdC6F5 and DMF (monoclinic, P21/n (no. 14)), while in the donor‐free compound (CDCl3 and H2O co‐crystallize) the cadmium atom is nearly ideally trigonal planar co‐ordinated (orthorhombic, Pbnm (no. 62)).

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Synthese und Eigenschaften von Diethyldithiocarbaminsäureperfluororganylestern, (C2H5)2NC(S)SRf (Rf = CF3, C2F5, i-C3F7, n-C4F9, C6F5)

Cited by 10 publications

References 12 publications

Gold trifluoromethyl complexes

Gold trifluoromethyl complexes

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

Syntheses, Characterizations, and Crystal Structures of β‐Diketiminato Compounds of Pentafluorophenyl Group 12 Derivatives, HC{[C(Me)N(C₆H₃‐2, 6‐i‐Pr₂)]₂}MC₆F₅ (M = Zn, Cd)

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Synthese und Eigenschaften von Diethyldithiocarbaminsäureperfluororganylestern, (C2H5)2NC(S)SRf (Rf = CF3, C2F5, i-C3F7, n-C4F9, C6F5)

Cited by 10 publications

References 12 publications

Gold trifluoromethyl complexes

Gold trifluoromethyl complexes

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

Syntheses, Characterizations, and Crystal Structures of β‐Diketiminato Compounds of Pentafluorophenyl Group 12 Derivatives, HC{[C(Me)N(C6H3‐2, 6‐i‐Pr2)]2}MC6F5 (M = Zn, Cd)

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Syntheses, Characterizations, and Crystal Structures of β‐Diketiminato Compounds of Pentafluorophenyl Group 12 Derivatives, HC{[C(Me)N(C₆H₃‐2, 6‐i‐Pr₂)]₂}MC₆F₅ (M = Zn, Cd)