160721-87-9

Upstream product

• 33603-89-3 (Z)-2-chloro-3-phenyl-2-propenal 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 13633-26-6 4-phenylbut-1-en-3-yne 
• 88307-34-0 (E)-2-methoxy-1-phenylbuta-1,3-diene 
• 88307-34-0 (Z)-2-Methoxy-1-phenyl-1,3-butadiene 
• 100-52-7 benzaldehyde 
• 24182-35-2 (E)-2-Bromo-1-phenyl-1,3-butadiene 

Relevant academic research and scientific papers

Chloroprene as a source of fine chemicals: Palladium-catalyzed synthesis of terminal allenes

(Equation presented) Several functionalized terminal allenes were prepared in moderate to excellent yield by a palladium-catalyzed reaction of chloroprene (2-chloro-1,3-butadiene) with soft nucleophiles.

Preparation of 2-chlorobuta-1,3-dienes by dichlorocyclopropanation of allylsilanes followed by desilylation

Allylsilanes react with dichlorocarbene to form dichloropropanes which, in turn, afford 2-chlorobuta-1,3-dienes when treated with cesium fluoride in DMF under reflux.The Z stereochemistry of the products differs from that of the starting allylsilanes.Lengthy reaction times were necessary to induce desilylation because of the lack of steric congestion in the intermediate silylmethyl-substituted cyclopropanes. 5-Methyl-7-trimethylsilylhepta-1,5-diene was cyclopropanated regioselectively at the inner ene function in spite of unfavourable steric congestion, possibly as a result of the electron-donating effect of the allylic silyl group induced by the ?-? conjugation.

Electronic and Conformational Effects in the Photochemistry of α-Alkenyl-Substituted Vinyl Halides

The photochemical reactions in methanol of the vinylic halides 2-halo-1-phenyl-1,3-butadienes 1-3Z-X (β-halo-β-alkenylstyrenes) and 1-halo-1,2-diphenylethenes 4Z-X (α-halostilbenes), with X = Cl or Br, have been studied quantitatively.E/Z isomerization, dehydrohalogenation, nucleophilic substitution, a -halogen shift, a -hydrogen shift, and oxidation are observed as the primary reactions.No reductive dehalogenation products are formed.The efficiencies of product formation are dependent on the halogen used, the electron-donating capacity of the α-substituent, the ground state conformation of the starting material, and the wavelength of excitation.Apart from the photoinduced E/Z isomerization and the oxidation reaction typical for alkenes, product formation occurs exclusively via vinyl-cationic intermediates, which are formed upon photolytic cleavage of the carbon-halogen bond.These ionic species, or part of them, are present as vinyl cation/halide anion-pairs.