Metal carbonyl-promoted reactions of ferrocenylacetylene with sulfur to form thiophene, dithiine, thioketone and vinylthioketone derivatives

Mathur, P. C.; Singh, Amrendra K.; Chatterjee, Saurav; Singh, Vinay; Mobin, Shaikh M.

doi:10.1016/j.jorganchem.2009.10.003

Cited by 11 publications

(3 citation statements)

References 33 publications

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“…Photochemical reactions of ferrocenylacetylene with sulfur in presence of Mo(CO)6 gives 2,5-diferrocenylthiophene and, with Cr(CO)6, 2,6-diferrocenyldithiine formed. Formation of ferrocenylsubstituted thioketone complexes was observed in the reaction of ferrocenylacetylene with water and sulfur, in presence of W(CO)6 [243]. Darensbourg reported the group 6 pentacarbonyl hydrides and various methods for their synthesis [244][245][246].…”

Section: In Synthesis Of Other Complexesmentioning

confidence: 99%

The chemistry of group-VIb metal carbonyls

Kaushik¹,

Singh²,

Kumar³

2012

Eur. J. Chem.

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KEYWORDSThe special interest attached to the chemistry of metal carbonyls arises from several causes. While quite distinct from the metal carbonyls in the organometallic compounds, they differ in physical properties (e.g., their volatility) from all other compounds of the transition metals. Chemically, they constitute a group of compounds in which the formal valency of the metal atoms is zero, and in this respect (apart, perhaps, from the ammoniates of the alkali metals) they are comparable only with the recently discovered compounds. As a class, the carbonyls are reactive compounds, and a number of new types of inorganic compounds have been discovered. In the concepts for new products, performance, product safety, and product economy criteria are equally important. They are taken into account already when the raw material base for a new industrial product development is defined. Since the discovery of nickel carbonyl by Mond and Langer in 1888, the carbonyls of the iron group and of chromium, molybdenum and tungsten have found important technical applications, e.g., in the Mond nickel process, and for the preparation of the metals in a state of subdivision and of purity suitable for powder metallurgy, for catalysts, etc. The reaction mechanism of the processes developed for producing the carbonyls technically has only recently received its interpretations. Within the space of review it is necessary to limit discussion to a few topics. Particular stress has accordingly laid upon (a) the chemical bonding in metal carbonyls, (b) importance of IR and NMR spectroscopy in characterization of metal carbonyls, (c) substitution reactions of G-VIb metal carbonyls, (d) kinetics and mechanism of substitution reactions in metal carbonyls, (e) substituted complexes of G-VIb metal carbonyl, (f) chelate complexes of G-VIb metal carbonyls, (g) uses of G-VIb metal carbonyl complexes and (h) studies done on G-VIb metal carbonyls.

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Section: In Synthesis Of Other Complexesmentioning

confidence: 99%

The chemistry of group-VIb metal carbonyls

Kaushik¹,

Singh²,

Kumar³

2012

Eur. J. Chem.

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“…Four crystal structures were found after a search for structures in which a Fc-group was bonded to a thiocarbonyl group and another substituent could be any moiety forming a C–C bond with this C=S group. These crystal structures are identified by the following CSD refcodes and chemical formulas: DUFYAG (C 18 H 18 Fe 1 N 2 O 1 S 2 ) [34], JEPVIJ (C 22 H 14 Cr 1 Fe 1 O 5 S 1 ) [35], VUTKAX (C 17 H 12 Fe 1 O 5 S 1 W 1 ) [36] and VUTKEB (C 29 H 22 Fe 2 O 5 S 1 W 1 ) [36]. Their molecular structures are shown in Figure S1 in the Supplementary Materials.…”

Section: Resultsmentioning

confidence: 99%

Structure of Diferrocenyl Thioketone: From Molecule to Crystal

et al. 2019

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Ferrocenyl-functionalized thioketones have recently been recognized as useful building blocks for sulfur-containing compounds with potential applications in materials chemistry. This work is devoted to a single representative of such thioketones, namely diferrocenyl thioketone (Fc2CS), whose structure has been determined here for the first time. Both X-ray crystallography and a wide variety of quantum-chemical methods were used to explore the structure of Fc2CS. In addition to the X-ray structure determination, intermolecular interactions occurring in the crystal structure of Fc2CS were examined in detail by quantum-chemical methods. These methods were also an invaluable tool in studying the molecular structure of Fc2CS, from the gas phase to solutions and to its crystal. Intramolecular interactions governing the conformational behavior of an isolated Fc2CS molecule were deduced from quantum-chemical analyses carried out in orbital space and real space. Our experimental and theoretical results indicate that the main structural features of an isolated Fc2CS molecule in its lowest-energy geometry are retained both upon solvation and in the crystal. The tilt of ferrocenyl groups is only slightly affected by crystal packing forces that are dominated by dispersion. Nonetheless, a network of intermolecular interactions, such as H···H, C···H and S···H, was detected in the Fc2CS crystal but each of them is fairly weak.

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“…Our work in this area has resulted in the synthesis of several new ferrocenyl containing metal carbonyl cluster compounds. [9][10][11][12][13][14][15][16][17][18] Previously, we have also reported that the reaction of an eneyne system (isopropenyl acetylene) with [Fe(CO) 5 ] in the presence of CO, yields the products 2,6-and 2,5-divinyl-substituted 1,4-benzoquinone. 19 In continuation of our work in the chemistry of ene-yne and ferrocenyl groups as substituents, our main goal has been to explore the reactivity of the multifunctional organotellurium (tellurium ene-yne) ligand bearing ferrocenyl groups, (Z)-1-ferrocenyltelluro-1-ferrocenyl-4-ferrocenyl-1buten-3-yne, with metal carbonyls for the formation and expansion of metallic clusters.…”

Section: Introductionmentioning

confidence: 99%

Some unusual reactions of metal carbonyls with (Z)-1-ferrocenyltelluro-1-ferrocenyl-4-ferrocenyl-1-buten-3-yne

Mathur

Tauqeer

et al. 2014

RSC Adv.

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The photolytic reaction of (Z)-1-ferrocenyltelluro-1-ferrocenyl-4-ferrocenyl-1-buten-3-yne with iron pentacarbonyl in hexane gives the tellurium coordinated carbonyl vinylallyl dinuclear iron complex 1, tellurium coordinated vinylallyl trinuclear iron complex 2, a lactone fused ferracyclopentadiene complex 3, and a butterfly complex 4. On reaction with PPh 3 , 1 undergoes fragmentation to yield a cyclopentadienone (7) and the starting material (Z)-1-ferrocenyltelluro-1-ferrocenyl-4-ferrocenyl-1buten-3-yne. In addition, reactions of the tellurium ene-yne ligand with [M(CO) 5 (THF)] or [M(CO) 6 ] give the M(CO) 5 adducts 8-10. All compounds have been characterized by IR, 1 H NMR and 13 C NMR spectroscopy and structures of 1-4 and 7 have been established by single crystal X-ray diffraction.

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Metal carbonyl-promoted reactions of ferrocenylacetylene with sulfur to form thiophene, dithiine, thioketone and vinylthioketone derivatives

Cited by 11 publications

References 33 publications

The chemistry of group-VIb metal carbonyls

The chemistry of group-VIb metal carbonyls

Structure of Diferrocenyl Thioketone: From Molecule to Crystal

Some unusual reactions of metal carbonyls with (Z)-1-ferrocenyltelluro-1-ferrocenyl-4-ferrocenyl-1-buten-3-yne

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