12154-63-1

Usage

Uses

Used in Organic Chemistry:
TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM is used as a catalyst for various organic chemistry reactions, particularly hydrogenation and carbonylation processes. Its selective catalytic ability allows for the efficient synthesis of specific organic compounds.
Used in Chemical Production:
TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM is utilized in the production of a range of organic compounds and materials, contributing to the development of various chemical products and industries.
Used in Research and Development:
TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM is employed in research settings to explore new synthetic pathways and improve existing ones, further enhancing the capabilities of synthetic chemistry.
It is crucial to handle TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM with caution due to the potential toxicity of chromium compounds, ensuring proper safety measures are in place during its use.

InChI:InChI=1/C10H12.3CO.Cr/c1-2-6-10-8-4-3-7-9(10)5-1;3*1-2;/h1-2,5-6H,3-4,7-8H2;;;;

Upstream product

• 119-64-2 tetralin 
• 12129-27-0 (η6-p-xylene)tricarbonylchromium(0) 
• 91-20-3 naphthalene 
• 199620-14-9 chromium⁽⁰⁾ hexacarbonyl 
• 130495-59-9 C₈H₆(O₂CH₂CH₂)Cr(CO)3 
• 624-49-7 dimethylfumarate 
• 14044-65-6 borane-THF 
• 12110-40-6 (η(6)-1,2-dihydronaphthalene)chromium tricarbonyl 
• 41371-94-2 tris(ammonia)chromium tricarbonyl 
• 108-90-7 chlorobenzene 

Downstream Products

• 157109-23-4 1-phenyl-(η(6)-1,2,3,4-tetrahydronaphthalene)chromiumtricarbonyl 
• 1245715-12-1 Cr(CO)3(η6-C6H4C4H7(C6H4CH3)) 
• 1245715-13-2 Cr(CO)3(η6-C6H4C4H7(C6H4N(CH3)2)) 
• 13577-40-7 1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone 
• 3160-17-6 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile 

Relevant academic research and scientific papers

Hydroboration, followed by water addition of benchrotrenic alkenes. Formal dihydrogen addition

The reaction of the BH3-THF reagent with benchrotrenic alkenes, followed by a water addition and the formation of hydrogenated products are described. This formation and the regioselectivity observed is a consequence of the electron withdrawing effect of the Cr(CO)3 group.

Chromium carbonyl complexes with aryl mono- and oligogermanes: Ability for haptotropic rearrangement

The intra- and intermolecular inter-ring η6 ? η6-haptotropic rearrangements (IRHR), occurring by involving interactions to Ge atoms in arylgermanes, were investigated theoretically and experimentally. The new methods for the synthesis of non-symmetrical polyaromatic Ge compounds were elaborated. Digermane Ph3GeGeMe2Cl (2) was obtained from Ph3GeGeMe2NMe2 (1) under action of Me3SiCl. Aryl digermane Ph3GeGeMe2(η6-C6H5)Cr(CO)3 (4) was obtained after lithiation of (η6-C6H6)Cr(CO)3 (3) with subsequent interaction with 2. It was established that thermally induced intramolecular IRHR in 4 is not observed experimentally; at similar reaction conditions in the presence of tetralin C10H12 (7) the bimolecular intermolecular IRHR occurs giving (η6-C10H12)Cr(CO)3 (8). DFT analysis of the intramolecular IRHRs for model germane (p-Tol)2Ge(H)(η6-Tol-p)Cr(CO)3 (MC1) and digermane Ph3GeGeH2(η6-C6H5)Cr(CO)3 (MC2) indicates a plausible effect of 3c-2e (agostic) Ge–H···Cr interaction on success of such rearrangement. The theoretical activation barrier is determined to be in the range of 35–37 kcal/mol. The model compound (η6-C6H3(GeHPh2)Me2-p)Cr(CO)3 (12) was obtained from (η6-C6H4Me2-p)Cr(CO)3 (11). The decomposition of 12 was observed under conditions of thermally induced IRHR. Molecular structures of 8, 11 and 12 in a crystal were investigated by XRD.

Palladium-catalyzed allylic substitution with (η6-Arene- CH2Z)Cr(CO)3-based nucleophiles

Although the palladium-catalyzed Tsuji-Trost allylic substitution reaction has been intensively studied, there is a lack of general methods to employ simple benzylic nucleophiles. Such a method would facilitate access to "α-2-propenyl benzyl" motifs, which are common structural motifs in bioactive compounds and natural products. We report herein the palladium-catalyzed allylation reaction of toluene-derived pronucleophiles activated by tricarbonylchromium. A variety of cyclic and acyclic allylic electrophiles can be employed with in situ generated (η6-C 6H5CHLiR)Cr(CO)3 nucleophiles. Catalyst identification was performed by high throughput experimentation (HTE) and led to the Xantphos/palladium hit, which proved to be a general catalyst for this class of reactions. In addition to η6-toluene complexes, benzyl amine and ether derivatives (η6-C6H5CH 2Z)Cr(CO)3 (Z = NR2, OR) are also viable pronucleophiles, allowing C-C bond-formation α to heteroatoms with excellent yields. Finally, a tandem allylic substitution/demetalation procedure is described that affords the corresponding metal-free allylic substitution products. This method will be a valuable complement to the existing arsenal of nucleophiles with applications in allylic substitution reactions.

Benzylic functionalization of (η6-alkylarene)chromium tricarbonyl complexes

A general method for the regioselective benzylic metallation of (η6-alkylarene)chromium tricarbonyl complexes on the action of lithium amides in THF under very mild conditions has been developed. Transmetallation reactions of the lithium derivatives thus obtained produce the corresponding benzylic organotin, zinc and copper chromium tricarbonyl complexes. Methods for the preparative benzylic functionalization of (η6-alkylarene)chromium tricarbonyl complexes have been developed, including carboxylation, α-hydroxyalkylation, γ-carbonylation, acylation, arylation, vinylation, heteroarylation and alkylation procedures. 5-Acetoxy-3-benzyl-1,4-methano-2,3,4,5-tetrahydro-1H-3-benzazepine has been prepared using the benzylic lithium derivative of the (η6-alkylarene)chromium tricarbonyl complex at the key step. This compound is a representative of the major class of physiologically active compounds known as C-norbenzomorphans.

The study of catalyst effects on the complexation of arenes with Cr(CO)6. An overview

New results from our thorough investigation of different catalystic effects on the rate and yields of complexation of arenes with Cr(CO) are presented with a short review of the subject.With decalin as solvent the following substances were found to be the best catalysts: butyl acetate, ethyl formate, and dimethyl succinate.Butyl acetate proved to be the catalyst also in di-n-butyl ether.Special attention was paid to the complexation of naphthalene, and chlorobenzene.Some unsuccessful attempts at asymmetric induction of complexation are also described.

Synthesis, Characterization, and Some Reactions of Tricarbonyl(cyclobutabenzene)chromium(0) Derivatives

The tricarbonyl(cyclobutabenzene)chromium(0) complexes 12-20, have been prepared from the free ligand and triammin-tricarbonylchromium(0) or hexacarbonylchromium(0).The complexes have been characterized by spectroscopic methods (IR, 1H NMR, 13C NMR) and mass spectrometry, and 1H-NMR signal assignments have been verified by an NOE experiment.Diastereomeric ratios have been determined by 1H NMR and the diasteromers of the 1-methyl derivative 16 separated by HPLC.A crystal-structure analysis is presented for exo-16.A photochemical ligand exchange takes place in 70percent yield for the 1-trimethylsilyl derivative 19.Metalation with n-butyllithium/tmeda at -78 deg C has been observed only for aromatic and not for the benzylic protons.

Chemistry of the podocarpaceae LXXI. Preparation, structure, and reactions of some (arene)tricarbonylchromium(0) complexes. Crystal structure of α-tricarbonylchromium(0)

Tricarbonylchromium(0) (7), tricarbonylchromium(0) (11) and (benzene)tricarbonylchromium(0) (10) were prepared and examined.Complex 7 was obtained as a mixture of diastereomers, an X-ray structural determination showing that the α-isomer possesses a near eclipsed conformation, in agreement with the conformation in solution deduced from 400 MHz 1H NMR analysis.Carbanions derived from 1,3-dithiane, 2-methyl-1,3-dithiane and 2-(2,2-dimethoxyethyl)-1,3-dithiane (24), and the dianion derived from 2,2'-methylenebis-1,3-dithiane (27) were prepared and brought into reaction with the complexes.Compounds 23 and 33 resulted from regioselective attack on 7 at the site predicted.Treatment with methyl electrophiles of the dithianyl η5-intermediate leading to 22 did not give products of acetyl incorporation.Arene lithiation-electrophilic quenching of 7 gave a mixture of compound 6 and its C(14) regioisomer along with the novel ketone 39 and its C(14) regioisomer.

Two-electron reduction of (η6-naphthalene)tricarbonylchromium. Haptotropic rearrangement to the (η4-naphthalene)tricarbonylchromiuin dianion

The electrochemical and chemical reduction of (η6-naphthalene)tricarbonylchromium is a two-electron ECE reduction. The chemical step is a haptotropic rearrangement, which leads ultimately to the (η4-naphthalene)tricarbonylchromium dianion. The dianion displays some unusual 13C NMR features that provide strong support for the proposed slip-fold mechanism. Reaction of the dianion with a proton source produces a (η5-cyclohexadienyl)tricarbonylchromium anion species, which can be oxidized to the original naphthalene complex. Molecular orbital arguments support the slip-fold mechanism. Finally, complete electrochemical reductive properties of the naphthalene complex are presented.