35293-95-9

Basic information

• Product Name: Propanedioic acid, methyl(1-phenylethenyl)-, diethyl ester
• CAS NO: 35293-95-9
• Molecular Formula: C16H20O4
• Molecular Weight: 276.332
• Mol File: 35293-95-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, methyl(1-phenylethenyl)-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, methyl(1-phenylethenyl)-, diethyl ester(35293-95-9)
• EPA Substance Registry System: Propanedioic acid, methyl(1-phenylethenyl)-, diethyl ester(35293-95-9)

Safety Data

• Hazardous Substances Data: 35293-95-9(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 609-08-5 Diethyl methylmalonate 
• 2181-42-2 trimethylsulphonium iodide 
• 5292-53-5 diethyl benzalmalonate 
• 74-88-4 methyl iodide 

Downstream Products

• 35205-58-4 ethyl 2-methyl-2-carboethoxy-3-phenylbutyrate 

Relevant articles and documents

Synthesis of ethyl 2-ethanoyl-2-methyl-3-phenylbut-3-enoate

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The unprecedented reaction of dimethylsulfonium methylide with Michael acceptors: Synthesis of 1-substituted vinyl silanes and styrenes

Rather than the usual cyclopropanation, conditions for an unprecedented elimination reaction from the adduct of dimethylsulfonium methylide and various Michael acceptors have been established leading to functionalized 1-substituted alkenes. In silyl substituted substrates (2a and 2h), where a facile Peterson-type olefination is possible from the adduct; elimination took place instead to give functionalized 1 -substituted vinyl silanes. Aryl substituted Michael acceptors (2b-e, 2g and 2i-k) also underwent a similar kind of olefination to give 1-substituted styrene derivatives with moderate yields along with a side product, which arose by nucleophilic demethylation from the adduct of dimethylsulfonium methylide and arylidene malonates. Hammett studies revealed that selectivity for olefination vs. demethylation increases as the aryl substituent becomes more electron deficient. Alkylidene malonates (2f and 2l) with a β-alkyl substituent did not favour the olefination process. Sequential addition of Michael acceptors and alkyl halides to a mixture of dimethylsulfonium methylide and sodium dimsylate provided olefination followed by alkylation on the active methine group. A mechanistic pathway has been formulated from the studies of a few sulfonium methylides. The Royal Society of Chemistry 2005.

A novel reaction of dimethylsulfonium methylide with Michael acceptors: Application to the synthesis of difficulty accessible vinyl silanes and styrenes

Rather than the usual cyclopropanation and Peterson-type olefination, conditions for a novel elimination reaction from the adduct of dimethylsulfonium methylide and 2-silylalk-ylidene/arylidene malonate/cyanoacetate/phosphonoacetate leading to geminally s