Reactivity of a two heteroatom stabilized anionic chromium (0) carbene complex towards a mono- and a disubstituted alkyne: New synthesis of γ-aminobutenolides and formation of a novel oligomer chromium (0) complex

Álvarez-Toledano, Cecilio; Baldovino, O.; Espinoza, G.; Toscano, Rubén A.; Gutiérrez-Pérez, René; García-Mellado, Olivia

doi:10.1016/s0022-328x(97)00091-0

Cited by 14 publications

(8 citation statements)

References 19 publications

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“…As in the structure of 2, in 3 and 4 too there is a lengthening of the complexed C@C bonds (C(8)-C(9) = 1.420(4) Å ; C(12)-C(13) = 1.418(4) Å in 3 and C(8)-C(9) = 1.424 (5) Å ; C(12)-C(13) = 1.417(4) Å ). This is consistent with observations previously made for g 4 -cyclopentadienone complexes that on g 4 -coordination, there is a loss of localized single and double bonding seen in free cyclopentadienones [23]. The unbridged Ru-Ru bonds in 3 and 4 (2.7417(4) and 2.7248(8) Å , respectively) are longer than the CO-bridged Ru-Ru bond in 2 (2.7104(8) Å ).…”

Section: Resultssupporting

confidence: 91%

Coupling reaction between the uncoordinated acetylenic bond of [Ru3(CO)10{μ3-FcC2CCFc}] and FcCCCCFc to form [Ru2(CO)6{C4Fc2(CCFc)2}2], [Ru2(CO)6[μ-η1:η1:η2:η2-{FcCCCC(Fc)–C(O)–C(Fc)CCCFc}] and [Ru2(CO)6[μ-η1:η1: η2:η2-{FcCCCC(Fc)–C(O)–C(–CCFc)C(Fc)}]

Mathur

Das

Chatterjee

et al. 2008

Journal of Organometallic Chemistry

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Section: Resultssupporting

confidence: 91%

Coupling reaction between the uncoordinated acetylenic bond of [Ru3(CO)10{μ3-FcC2CCFc}] and FcCCCCFc to form [Ru2(CO)6{C4Fc2(CCFc)2}2], [Ru2(CO)6[μ-η1:η1:η2:η2-{FcCCCC(Fc)–C(O)–C(Fc)CCCFc}] and [Ru2(CO)6[μ-η1:η1: η2:η2-{FcCCCC(Fc)–C(O)–C(–CCFc)C(Fc)}]

Mathur

Das

Chatterjee

et al. 2008

Journal of Organometallic Chemistry

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“…Likewise, the experimental geometry of cyclopentadienone has not been observed directly but as a subunit of its tetraphenyl derivative. 59 Here too, the calculated and observed bond length and angles agree within 2 pm and 2 degrees, respectively. To the authors best knowledge the geometry of cyclopentadienethione has not been determined by experimental techniques.…”

Section: A Geometriessupporting

confidence: 57%

Static electric properties of conjugated cyclic ketones and thioketones

Eckart¹,

Fülscher²,

Serrano‐Andrés³

et al. 2000

The Journal of Chemical Physics

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Articles you may be interested inHow large is the static electric (hyper)polarizability anisotropy in HXeI?The results of ab initio calculations of static electric properties of a series of cyclic conjugated ketones and thioketones are presented. Dipole moments, dipole polarizabilities, as well as the first and second hyperpolarizabilities, were evaluated at different levels of theory: SCF, CASSCF, MP2, CCSD, CCSD͑T͒, and CASPT2 methods were used. Both MP2 and CASPT2 methods have been shown to perform well in the calculation of such properties. The dependence of the electric properties on the extent of the -electron conjugation and on the replacement of the keto by the thioketo group is analyzed. Cyclic conjugated thioketones are shown to exhibit significant nonlinear electric properties which make them prospective building blocks for nonlinear optical materials.

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“…The paddle-wheel conformation is also a typical feature of the parent substance tetraphenylcyclone (Barnes et al, 1991;Alvarez-Toledano et al, 1997) and the related compound phencyclone (Ruffani et al, 2006), both involving C-HÁ Á Á contacts in the crystal packing, similar to the title compound. For related literature, see: Dilthey et al (1935).…”

Section: Related Literaturementioning

confidence: 84%

3,4-Bis(4-bromophenyl)-2,5-diphenylcyclopenta-2,4-dienone

Schwarzer

Weber

2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 93 K; mean (C-C) = 0.003 Å; R factor = 0.019; wR factor = 0.047; data-to-parameter ratio = 13.8.The title compound, C 29 H 18 Br 2 O, crystallizes as black-violet plates. The molecule displays a paddle-wheel conformation and the crystal packing is stabilized by C-HÁ Á Á (C-HÁ Á Á distances in the range 2.7-2.9 Å ) and C-HÁ Á ÁBr contacts. organic compounds o3966 # 2007 International Union of Crystallography 3,4-Bis(4-bromophenyl)-2,5-diphenylcyclopenta-2,4-dienone A. Schwarzer and E. Weber CommentThe molecular geometry is best described by a paddle-wheel fashion, due to steric hindrance of the neighbouring aryl rings.The crystal packing is dominated by intramolecular C-H···π interactions. These intermolecular contacts, where π is an aromatic-ring centroid, with H···π distances ranging from 2.67 to 2.90 Å give rise to the formation of molecular chains extended along the a and b axis. Furthermore, unusual C-H···Br contacts forming a three-dimensional network can be observed (Figure 2). ExperimentalThe title compound was synthesized according to the procedure described by Dilthey et al. (1935) from 1,2-bis(4-bromophenyl) ethane-1,2-dione, dibenzyl ketone and finely powdered potassium hydroxide in ethanol. Recrystallization from ethyl acetate yielded 72% dark-violet crystals. RefinementThe H atoms were positioned geometrically and allowed to ride on their parent atoms, with C-H = 0.95 Å, and U iso = 1.2-1.5 U eq (parent atom).

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Reactivity of a two heteroatom stabilized anionic chromium (0) carbene complex towards a mono- and a disubstituted alkyne: New synthesis of γ-aminobutenolides and formation of a novel oligomer chromium (0) complex

Cited by 14 publications

References 19 publications

Coupling reaction between the uncoordinated acetylenic bond of [Ru3(CO)10{μ3-FcC2CCFc}] and FcCCCCFc to form [Ru2(CO)6{C4Fc2(CCFc)2}2], [Ru2(CO)6[μ-η1:η1:η2:η2-{FcCCCC(Fc)–C(O)–C(Fc)CCCFc}] and [Ru2(CO)6[μ-η1:η1: η2:η2-{FcCCCC(Fc)–C(O)–C(–CCFc)C(Fc)}]

Coupling reaction between the uncoordinated acetylenic bond of [Ru3(CO)10{μ3-FcC2CCFc}] and FcCCCCFc to form [Ru2(CO)6{C4Fc2(CCFc)2}2], [Ru2(CO)6[μ-η1:η1:η2:η2-{FcCCCC(Fc)–C(O)–C(Fc)CCCFc}] and [Ru2(CO)6[μ-η1:η1: η2:η2-{FcCCCC(Fc)–C(O)–C(–CCFc)C(Fc)}]

Static electric properties of conjugated cyclic ketones and thioketones

3,4-Bis(4-bromophenyl)-2,5-diphenylcyclopenta-2,4-dienone

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