C–S bond cleavage in pyridylmethylthioether systems promoted by oxorhenium(V) ion

Das, Biswajit; Sarkar, Sandipan; Zangrando, Ennio; Chattopadhyay, Pabitra

doi:10.1016/j.inoche.2009.08.035

Cited by 8 publications

(7 citation statements)

References 43 publications

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“…The two free radicals can then recombine into dps. The in situ S-C bond Copper complexes with sulfur-bridged bis-pyridine 3183 cleavage was also reported for pyridylmethylthioether, leading to formation of Cu(II) picolinate derivatives or oxorhenium(V) complexes of 2-(2-pyridylmethyl)ethane-1-thiol [35][36][37].…”

Section: Plausible Mechanism For Formation Of 1 Andmentioning

confidence: 68%

Three copper complexes containing the sulfur-bridged bis-pyridine ligands, 2,2′-dithiodipyridine and di-2-pyridyl sulfide

Pan

Zhou

Wang

et al. 2014

Journal of Coordination Chemistry

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Three copper complexes constructed with sulfur-bridged bis-pyridine ligands 2,2′-dithiodipyridine (dtdp) and di-2-pyridyl sulfide (dps), [Cu 2 (dps) 2 (H 2 O) 2 (μ-SO 4 ) 2 ]·(H 2 O) 2 (1), [Cu 2 I 2 (dps) 2 ] (2), and [Cu 4 I 4 (dtdp) 2 ] (3), have been synthesized by reaction of copper(I) iodide with dtdp under solvothermal and solution-diffusion conditions, and characterized by single crystal X-ray diffraction. The dps ligands were generated via in situ cleavage of S-S and S-C(py) bonds of dtdp. Cu ions are divalent in 1, implying involvement of the starting Cu + cations in a redox process, while the Cu ions remained univalent in 2 and 3. In 1 and 2, the dps adopted N,N-chelate coordination, in contrast to the N,Schelation of the dtdp ligand in 3. Complex 1 displays a 2-D framework linked by hydrogen bonds and was further connected into a 3-D supramolecular structure by π-π stacking interactions between adjacent layers. Complexes 2 and 3 exhibited 2-D layer structures through π-π stacking interactions. The luminescent properties of 2 and 3 were also studied in the solid state at room temperature.

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Section: Plausible Mechanism For Formation Of 1 Andmentioning

confidence: 68%

Three copper complexes containing the sulfur-bridged bis-pyridine ligands, 2,2′-dithiodipyridine and di-2-pyridyl sulfide

Pan

Zhou

Wang

et al. 2014

Journal of Coordination Chemistry

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“…In this section, only a concise overview of C-S bond cleavage by stoichiometric amounts of transition metal compounds is presented although a variety of reports have been documented in this area. [1][2][3][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Coordination models of thiophene rings to transition metals have been reported, demonstrating diverse C-S bond activation in the complexes (Scheme 1). 31 In particular, the insertion reactions of metal atoms to C-S bonds in thiophenes and other organosulfur compounds have been extensively studied in order to get better understanding of the heterogeneous HDS mechanisms.…”

Section: C-s Bond Activation By Stoichiometric Transition Metal Compo...mentioning

confidence: 99%

Transition-metal mediated carbon–sulfur bond activation and transformations

2013

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C-S bond activation, cleavage and transformations by means of transition metal compounds have recently become more and more important in the petroleum industry and synthetic chemistry. Homogeneous transition metal compounds have been investigated in order to provide the fundamental insight into the C-S bond cleavage in problematic organosulfur compounds such as thiophene, benzo- and dibenzothiophene derivatives. Rendering transition-metal mediated reactions with organosulfur compounds catalytic may provide promising routes to deep hydrodesulfurization of petroleum feedstocks, and offer potentially useful synthetic protocols for cross-couplings and biomimetic organic synthesis. During the last few decades increasing work was documented on C-S bond activation and transformations by means of transition metal compounds. This review summarizes the recent advances in C-S bond cleavage via the insertion of transition metals into the inert C-S bonds of these problematic organosulfur compounds, and transition-metal mediated C-S bond transformations via C-S activation through cross-couplings of thioesters, ketene dithioacetals, sulfonyl chlorides, and other diverse organosulfur compounds.

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“…1, and selected bond lengths and angles have been tabulated in Table 2. The rhenium atom displays a distorted octahedral geometry and is chelated by the tridentate seleniumbis(phenato) ligand and by the bidentate selenium(methylenechloride)phenato ligand in such a way that the chal- and 164.33 (15)°of O(2)-Re-Se (2). The presence of tertbutyl groups at the phenyl rings hampers the formation of p-p interactions in the crystal packing.…”

Section: Resultsmentioning

confidence: 99%

“…The contribution of H atoms at calculated position was included in the final cycles of refinement. The tert-butyl group bound to C16 was found to be disordered over two positions with refined occupancies of 0.525(15)/475 (15). These atoms were isotropically refined by restraining the same distance between the quaternary C and methyl groups.…”

Section: X-ray Crystallographymentioning

confidence: 99%

“…As a continuation of our interest in new oxorhenium(V) complexes of different polydentate chelators [12][13][14][15][16] and considering the above synthetic strategy here, a new seleno-bonded ternary mononuclear oxorhenium(V) complex of 2,2 0 -selenobis(4,6-di-tert-butylphenolate) (L 1 ) and in situ formed 2-selenochloromethyl-4,6-di-tert-butylphenolate (L 2 ) formulated as [ReO(L 1 )(L 2 )] has been synthesized by a solvothermal reaction and characterized using physicochemical and spectroscopic tools. The detailed structure has been established by X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

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A selenium-bonded oxorhenium(V) complex: solvothermal synthesis, structural characterization, and electrochemical behavior

Das

Chakraborty

Sarkar

et al. 2011

Transition Met Chem

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The solvothermal reaction of [ReOCl 3 (PPh 3 ) 2 ] with 2,2 0 -seleno-bis(4,6-di-tert-butylphenol) (H 2 L 1 ) in ethanol at 95°C resulted in an oxorhenium(V) complex of formulation [ReO(L 1 )(L 2 )] due to the in situ formation of 2-selenochloromethyl-4,6-di-tert-butylphenolate (L 2 ) through the cleavage of one C-Se bond of H 2 L 1 . The mononuclear oxorhenium(V) complex was characterized by physicochemical and spectroscopic methods along with detailed structural analysis by single crystal X-ray crystallography. Electrochemical studies revealed a one-electron equivalent quasi-reversible voltammogram for the ReO(V)/ ReO(VI) redox couple at 1.28 V (versus SCE) with no cathodic response for ReO(V) ? ReO(IV) reduction.

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C–S bond cleavage in pyridylmethylthioether systems promoted by oxorhenium(V) ion

Cited by 8 publications

References 43 publications

Three copper complexes containing the sulfur-bridged bis-pyridine ligands, 2,2′-dithiodipyridine and di-2-pyridyl sulfide

Three copper complexes containing the sulfur-bridged bis-pyridine ligands, 2,2′-dithiodipyridine and di-2-pyridyl sulfide

Transition-metal mediated carbon–sulfur bond activation and transformations

A selenium-bonded oxorhenium(V) complex: solvothermal synthesis, structural characterization, and electrochemical behavior

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