702-90-9

Upstream product

• 839-39-4 cyclopropane-1,1,2-tricarboxylic acid triethyl ester 
• 33626-79-8 1-acetyl-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 65590-89-8 ethyl 1-cyano-2-vinylcyclopropane-1-carboxylate 
• 685-87-0 Diethyl 2-bromomalonate 
• 107-13-1 acrylonitrile 
• 140-88-5 ethyl acrylate 
• 75911-83-0 1-ethyl 2-methyl 1-(2-methoxyacetyl)cyclopropane-1,2-dicarboxylate 
• 3674-13-3 2,3-dibromopropionic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 144829-35-6 Dimethyl 2-methoxycarbonyl-3-methylenesuccinate 
• 876488-15-2 3-bromo-propane-1,1,2-tricarboxylic acid trimethyl ester 
• 67-56-1 methanol 
• 22650-26-6 trimethyl cyclopropane-1,1,2-tricarboxylate 
• 7664-93-9 sulfuric acid 

Downstream Products

• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 305377-31-5 1-trifluoromethyl-cis-1,2-cyclopropanedicarboxylic acid 
• 53358-22-8 (Z)-γ-methylglutaconic acid 
• 5621-44-3 dimethyl 2-methylenepentanedioate 
• 114644-54-1 cis-1-hydroxymethylcyclopropane-1,2-dicarboxylic acid 
• 114644-57-4 dimethyl cis-1-(p-tolylsulphonyloxymethyl)cyclopropane-1,2-dicarboxylate 

Relevant academic research and scientific papers

Synthesis, thermal, mass and ab initio analyses of cyclopropane-1,1,2- tricarboxylic acid

The preparation of cyclopropane-1,1,2-tricarboxylic acid from cyanoacetic acid and 2,3-dibropropionic acid has been done in one-step procedure in alkaline medium. The compound has been characterized, by nuclear magnetic resonance, mass spectrometry, and t

Carbon-13 Labelling Study of the Coenzyme B12-dependent Methylitaconate α-Methyleneglutarate Model Rearrangement Reaction and Examination of Potential Cyclopropane Intermediates

The model rearrangement mimicking the coenzyme B12-dependent, enzyme-catalysed interconversion of α-methyleneglutaric acid with methylitaconic acid has been carried out with a carbon-13 label.This experiment demonstrates beyond doubt that the acrylate group is the migrating group in the model, as it is in the enzyme-catalysed rearrangement.Experiments designed to probe the possible occurence of cyclopropylmethyl intermediates in the model rearrangement are also described.To this end the cis- and trans-bromomethylcyclopropanediacids (16a) and (20a) were prepared starting from the common precursor cyclopropane-1,1,2-tricarboxylic acid (13).Thus, (13) was converted into the anhydride (14) which was, in turn, reduced to the lactone (15).Opening of the lactone with HBr in acetic acid gave the desired trans-diacid (16a).For the cis-diacid (20a), the anhydride (14) was hydrolysed, esterified with diazomethane, then reduced with lithium triethylborohydride.Conversion of the resulting alcohol (19) into the bromide (20a) was effected with phosphorus tribromide.An extensive series of experiments involving treatment of the acids and their methyl and tetrahydropyranyl esters with vitamin B12s was carried out.No methylitaconic acid (3a) could be detected in any of the reaction mixtures.However, α-methyleneglutaric acid (2a) and methylglutaconic acid (21) were observed as the reaction products.The methyl toluene-p-sulphonate (22) and iodide (23) were also examined and yielded results analogous to those obtained with the bromides.

CYCLOPROPANE-1,1 prime -INDENES.

The relative concentrations of stereoisomers in product mixtures were determined as a function of time by using a combination of analytical techniques: vapor phase chromatography, polarimetry, NMR spectroscopy, and NMR spectroscopy in the presence of an optically active lanthanide shift reagent. The stereochemical reaction kinetics reveal that the Smith mechanism is not a plausible model for one-center epimerization; two trimethylenes, produced through two distinct cyclopropane C-C bond cleavages, are implicated, since all three possible one-center epimerizations are seen.