331969-32-5

Usage

General Description

1,2-bis(4-(trifluoromethoxy)phenyl)ethane-1,2-dione is a complex organic compound with two ethane-1,2-dione groups attached to a central 1,2-bis(4-(trifluoromethoxy)phenyl)ethane core. It is commonly referred to as TFEDA and is used as a precursor in the synthesis of various organic compounds. TFEDA has a high degree of stability and is resistant to hydrolysis, making it a valuable reagent in organic chemistry. It is also used as a building block for the production of agrochemicals, pharmaceuticals, and specialty chemicals due to its unique structure and reactivity. Additionally, TFEDA is used as a ligand in coordination chemistry and as a stabilizer for certain industrial processes.

Upstream product

• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 103962-05-6 1-iodo-4-(trifluoromethoxy)benzene 

Relevant academic research and scientific papers

Phosphorus(III)-Mediated, Tandem Deoxygenative Geminal Chlorofluorination of 1,2-Diketones

Tetrasubstituted carbon containing two different halogen substituents was constructed in a single-step operation by utilizing the carbene-like reactivity of dioxaphospholene through the tandem reaction of electrophilic and nucleophilic halogenating reagents. It was crucial to devise non-dealkylatable phosphoramidite, which enabled the efficient formation of geminal chlorofluorides from various 1,2-diketones with (PhSO2)2NF and n-Bu4NCl. In addition, selective functionalization of the chlorine substituent was demonstrated, and the absence of halogen scrambling was confirmed.

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

Reactions of 1,2-diketones with vinyllithium: Addition reactions and dianionic oxy Cope rearrangements of cyclic and acyclic substrates

Dianionic oxy Cope rearrangements have been shown to take place at low temperature upon syn double addition of alkenyllithium derivatives to cyclobutanedione compounds such as benzocyclobutenedione chromium complex 1 or squaric acid esters. In order to obtain some insight into the more general applicability of this type of reaction sequence beyond these special cases, a number of 1,2-diketones were treated with vinyllithium. The diketones tested include benzil derivatives, aliphatic acyclic 1,2-diketones, ortho-quinones, and cyclic aliphatic 1,2-diketones. With benzil and heterobenzil derivatives, the desired double addition/dianionic oxy Cope rearrangement was found to take place at low temperature, leading to 1,6-diketones and their intramolecular aldol adducts in up to 80% overall yield. With acyclic aliphatic 1,2-diketones as substrates, this reaction sequence was also found, albeit with somewhat lower yields and requiring higher temperatures than in the benzil cases. A brief investigation of the intramolecular aldol adduct/1,6-hexanedione equilibrium indicated that the preferential formation of intramolecular aldol adducts at lower temperatures and at shorter reaction times appears to be the result of kinetic reaction control, whereas the preference for 1,6-diketones at higher temperatures is caused by thermodynamic reaction control, ortho-Quinones reacted with vinyllithium only by addition; no dianionic oxy Cope rearrangement was observed. This was also the case for most aliphatic cyclic diketones; however, in the case of 1,2-indanedione, rearrangement products were obtained in moderate yield at elevated reaction temperatures.