19952-65-9

Basic information

• Product Name: t-3-Phenyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester
• Synonyms: t-3-Phenyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester
• CAS NO: 19952-65-9
• Molecular Weight: 234.252
• Mol File: 19952-65-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: t-3-Phenyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester(CAS DataBase Reference)
• NIST Chemistry Reference: t-3-Phenyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester(19952-65-9)
• EPA Substance Registry System: t-3-Phenyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester(19952-65-9)

Safety Data

• Hazardous Substances Data: 19952-65-9(Hazardous Substances Data)

Upstream product

• 4165-96-2 3-phenylglutaric acid 
• 19329-22-7 (+/-)-5t-phenyl-4,5-dihydro-1H-pyrazole-3,4r-dicarboxylic acid dimethyl ester 
• 19329-22-7 (+/-)-5c-phenyl-4,5-dihydro-1H-pyrazole-3,4r-dicarboxylic acid dimethyl ester 
• 19329-23-8 (+/-)-4t-phenyl-4,5-dihydro-1H-pyrazole-3,5r-dicarboxylic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 19952-66-0 (1RS,2RS,3RS)-3-Phenylcyclopropane-1,2-dicarboxylic acid 
• 103548-67-0 (Dimethylsulfuranyliden)essigsaeure-methylester 
• 103-26-4 Methyl cinnamate 
• 96-34-4 methyl chloroacetate 
• 19952-64-8 3t-phenyl-cyclopropane-1r,2c-dicarboxylic acid 

Downstream Products

• 139156-62-0 (1R,2S,3S)-2-(Methoxycarbonyl)-3-phenylcyclopropane-1-carboxylic acid 
• 139156-62-0 (1S,2R,3R)-2-(Methoxycarbonyl)-3-phenylcyclopropane-1-carboxylic acid 
• 119945-25-4 C₁₁H₁₄N₄O₂ 
• 5682-61-1 (1S,2S)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 19952-66-0 (1RS,2RS,3RS)-3-Phenylcyclopropane-1,2-dicarboxylic acid 

Relevant articles and documents

Reactions of stabilized sulfur ylides with α,β-unsaturated alkoxychromiumcarbene complexes

Reaction of stabilized sulfur ylides with α,β-unsaturated alkoxy-chromiumcarbene complexes in MeCN as solvent forms vinylenol ethers 3, cyclopropanes 4, and vinylcyclopropanes 5, depending on the reagent ratio, the temperature and the nature of the ylide. The results obtained in these reactions suggest that factors apart from steric hindrance may control the chemoselectivity of the addition. Less stable ylides would add preferentially to the carbene carbon, 1,4-addition increasing as the stability of the ylide does. For more stable ylides 1,4-addition is preferred and substitution at the β-carbon has little effect in the chemoselectivity. Methoxycarbonylmethylentriphenylphosphorane exclusively add to the carbene carbon while ethyl diazoacetate is unreactive towards α,β-unsaturated alkoxychromium-carbene complexes in the conditions studied.

Cyclopropanediamines, 3. - Pure Diastereomers of 1,2-Cyclopropanedicarboxylic Acids and Derivatives

Efficient preparations of pure diastereomers of dimethyl 1,2-cyclopropanedicarboxylates 2, dicarboxylic acids 3, dicarbonyl dichlorides 4, and dihydrazides 5 are reported.Mixtures of diastereomers of dimethyl dicarboxylates 2a, b, d, e are obtained from α,β-unsaturated methyl carboxylates 7 and methyl α-chlorocarboxylates 8 as well as from 7c, d and the sulfur ylide 10 (2c, d).The diastereomers are separated by fractionating distillations (2a, b, c, e) or crystallization (2d) on a 100-g to 1-kg scale (d.e. >99percent).Only low yields of 2c are obtained in the reaction of methyl crotonate (7c) with methyl α-chloroacetate (8a), since 7c predominantly dimerizes to afford 12.The diesters 2 are converted into the pure diastereomeric diacids 3, dicarbonyl dichlorides 4, and dihydrazides 5. 3,3-Dimethyl-cis-1,2-cyclopropanedicarboxylic acid (cis-3f) is obtained by trans-->cis isomerization of trans-3f with the help of acetic anhydride and sodium acetate as catalyst.The configurations of 2-6 and 12 are confirmed by 1H NMR spectroscopy.Derivatives of cis-1,2-dimethyl-1,2-cyclopropanedicarboxylic acid tend to form bicyclic products.Thus, the reaction of cis-3e with phosphorus pentachloride yields mainly the cyclic anhydride 6e and only small amounts of the dicarbonyl dichloride cis-4e.Furthermore, the dihydrazide cis-5e slowly cyclizes in the solid state to give the N-aminoimide 13 and hydrazine, a reaction which is fast in solution.Pure 13 is obtained by thermolysis of cis-5e at 60-65 deg C under high vacuum.