Sodium phenyl -2-propenoate

Exercise 18-48 The Michael-addition product that results from ethyl 3-phenyl-propenoate and diethyl propanedioate, in principle, also can be formed by sodium ethoxide-catalyzed addition of ethyl ethanoate to ethyl (2-carbethoxy)-3-phenyl-propenoate. Work out the course of this reaction along the lines of Equations 18-25 and 18-26 and explain why it is less likely to be successful than the addition of diethyl propanedioate to ethyl 3-phenylpropenoate. It will be helpful to compare the various possible acid-base equilibria involved in the two possible routes to the same Michael-addition product. 

In the Pschorr synthesis (Scheme 12.12), a Perkin reaction (see Chapter 6) between 2-nitrobenzaldehyde and sodium phenylacetate in the presence of acetic anhydride yields 3-(2-nitrophenyl)-2-phenyl-propenoic acid. Reduction of the nitro group and deamination of the resulting amine via its diazonium salt (see Chapter 8) is accompanied by cyclization. Thermal decarboxylation completes the sequence. 

Methyl 2-[3-(trifluoromethyl)phenyl]-4/7-furo[3,2-4]pyrrole-5-carboxylate 81a was made by thermolysis of the corresponding methyl 2-azido-3- 5-[3-(trifluoromethyl)phenyl]-2-furyl propenoate 378, which was formed by condensation of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde 377 with methyl azidoacetate under sodium meth-oxide catalysis (Scheme 40) <2006KGS825>. 

See Styrene/butadiene polymer Ethenylbenzene, polymer with 2-propenamide. See Styrene/acrylamide copolymer Ethenylbenzenesulfonic acid, sodium salt, homopolymer 4-Ethenylbenzenesulfonic acid sodium salt, homopolymer. See Sodium polystyrene sulfonate 4-Ethenylcyclohexene 4-EthenyM -cyclohexene. See 4-Vinylcyclohexene Ethenyidimethoxymethylsilane. See Vinylmethyidimethoxysilane 1 -Ethenyl-1,5-dimethyl-4-hexenyl benzeneacetate. See Linalyl phenylacetate 1 -Ethenyl-1,5-dimethyl-4-hexenyl 3-phenyl-2-propenoate. See Linalyl cinnamate Ethenyl ethanoate. See Vinyl acetate 6-Ethenyl-6-(methoxyethoxy)-2,5,7,10-tetraoxa-6-silaundecane. SeeVinyltris(2-methoxyethoxy) silane... 

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