Chlorodicarbonylrhodium dimer

Base Information

• Chemical Name: Chlorodicarbonylrhodium dimer
• CAS No.: 14523-22-9
• Molecular Formula: C₄Cl₂O₄Rh
• Molecular Weight: 285.853
• Hs Code.: 28439000
• UNII: CRZ1K8LPMR
• Mol file: 14523-22-9.mol

Synonyms:CRZ1K8LPMR;Chlorodicarbonylrhodium dimer;(RH(CO)2CL)2;Tetracarbonyldi-mu-chlorodirhodium;.mu.-Dichlorotetracarbonyldirhodium;CHLORORHODIUM DICARBONYL DIMER;(RH(CO)2(.MU.-CL))2;Di-.mu.-chloro-bis(dicarbonylrhodium);DICARBONYLRHODIUM CHLORIDE DIMER;RHODIUM CARBONYL CHLORIDE [MI];NSC-120116;Rhodium, tetracarbonyldi-.mu.-chlorodi-;BIS(DICARBONYL(.MU.-CHLORO)RHODIUM);TETRACARBONYL-.MU.,.MU.'-DICHLORODIRHODIUM(I)

Chemical Property of Chlorodicarbonylrhodium dimer

Chemical Property:

• Appearance/Colour: crystalline
• Melting Point: 120-125
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 0.54700
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Solubility.: It is soluble in organic or non-aqueous solvent.
• Water Solubility.: soluble in most organic solvents; insoluble aliphatic hydrocarbons [MER06]
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 387.72835
• Heavy Atom Count: 12
• Complexity: 10

Purity/Quality:

99%, ^*data from raw suppliers

RhodiumCarbonylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 36/38-25
• Safety Statements: 22-24/25-37/39-28A-26-15

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Cl-].[Cl-].[Rh].[Rh]
• General Description: Rhodium carbonyl chloride, also known as [Rh(CO)2Cl]2, is a highly effective catalyst for tandem reactions involving 1,3-acyloxy migration and [5 + 1] cycloaddition with carbon monoxide, enabling the synthesis of functionalized cyclohexenones from cyclopropyl-substituted propargyl esters. Its catalytic activity facilitates both migration and carbonylation steps, demonstrating high efficiency and regioselectivity in the formation of complex molecular structures. Rhodium carbonyl chloride's role in optimizing reaction conditions and yielding alkylidene cyclohexenones highlights its utility in synthetic organic chemistry.

Refernces

Rhodium-catalyzed carbonylation of cyclopropyl substituted propargyl esters: A tandem 1,3-acyloxy migration [5 + 1] cycloaddition

10.1021/jo300973r

The research focuses on the development of novel tandem reactions for the synthesis of highly functionalized cyclohexenones from cyclopropyl substituted propargyl esters, utilizing rhodium-catalyzed 1,3-acyloxy migration followed by a [5 + 1] cycloaddition with carbon monoxide (CO). The study explores the reactivity of various transition metal catalysts, with a particular emphasis on the use of [Rh(CO)2Cl]2, which facilitates both the 1,3-acyloxy migration and the carbonylation reaction. The experiments involved treating propargyl esters with different catalysts and optimizing reaction conditions to achieve high yields of the desired alkylidene cyclohexenone products. The analyses used to characterize the products and intermediates included nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and high-resolution mass spectrometry (HRMS). The research also investigated the regioselectivity of the reaction and the influence of substrate stereochemistry on the reaction outcome, providing insights into the mechanism of the tandem reaction and its potential applications in the synthesis of complex molecular structures.

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