42198-68-5

Upstream product

• 140-10-3 cis-cinnamic acid 
• 55836-65-2 methyl (α-deuterio)cinnamate 
• 21788-36-3 (Z)-methyl 2-bromo-3-phenylacrylate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 100-52-7 benzaldehyde 
• 122570-52-9 (2-carboxy-1-phenylethenyl-2-d)tris(3-sulfophenyl)phosphonium inner salt, trisodium salt 

Downstream Products

• 30833-66-0 2-deuterio-2-oxo-acetic acid 
• 100-52-7 benzaldehyde 
• 473469-85-1 C₂₀H₁₅⁽²⁾HO₄ 
• 1279102-35-0 α-D-(E)-cinnamoyl fluoride 
• 370558-37-5 N-(2-iodo-4-methylphenyl)-N-benzyl-(α-deuterio)cinnamide 
• 370558-28-4 3-hydroxy-1,3-dibenzyl-5-methylindolin-2-one 
• 370558-21-7 1,3-dibenzyl-5-methylindolin-2-one 
• 81509-22-0 acide<²H>-2 phenyl-3 endo bicyclo<2.2.1> heptene-5 carboxylique-2 exo<²H> 
• 81509-22-0 acide<²H>-2 phenyl-3 exo bicyclo<2.2.1> heptene-5 carboxylique-2 endo <²H> 

Relevant academic research and scientific papers

Mechanism leading to the observed product of intramolecular aryl Diels-Alder reaction

A mechanistic investigation into the recently reported intramolecular aryl Diels-Alder reaction was carried out using deuterium labeling. These studies led to the conclusion that the initial Diels-Alder adduct is isomerized to a highly conjugated tetra-ene intermediate which undergoes a stereospecific suprafacial 1,5-dienyl hydrogen shift to give the observed product.

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.

ORGANIC CHEMISTRY IN WATER (PART V) NUCLEOPHILIC ADDITION OF WATER-SOLUBLE PHOSPHINES ON ACTIVATED ALKYNES: AN EFFICIENT SYNTHESIS OF NEW VINYLPHOSPHONIUM SALTS AND OF SPECIFICALLY DEUTERATED OLEFINS.

Triphenylphosphine m-trisulfonate 1 and triphenylphosphine m-monosulfonate 2 react in water with activated alkynes R-CC-A (A = CO2H, CO2R1, COR2, CHO) affording new vinylphosphonium salts or vinylphosphine oxides or alkenes depending on the pH of the aqueous solution and on the nature of the substituent R.The reactions of 1 or 2 with alkynes bearing an electron-acceptor substituent R give rise to the corresponding trans disubstituted olefins.Specifically mono or dideuterated alkenes are thus obtained in good yields by sequential use of H2O-D2O.When R = H or Alkyl, vinylphosphonium salts or vinylphosphine oxides are quantitatively produced respectively in acidic or in neutral solution.

Vinyl Anions. Part 9. Vinyl Carbanions Derived from Acrylic Esters and their β-Phenyl Derivatives

Ethyl ββ-diphenylacrylate, ethyl cis- and trans-cinnamate, methyl and ethyl maleate, ethyl fumarate, and methyl acrylate were treated with a strong base at low temperatures to yield the derived vinyl carbanions.The vinyl carbanions were treated with vario