948-98-1

Upstream product

• 100-34-5 benzene diazonium chloride 
• 536-74-3 phenylacetylene 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 109391-85-7 C₂₀H₁₇Cl₃Se 
• 501-65-5 diphenyl acetylene 
• 948-99-2 α-chloro-(Z)-stilbene 
• 947-90-0 2,2-diphenyl-vinylamine 
• 56-23-5 tetrachloromethane 
• 451-40-1 phenyl benzyl ketone 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 947-91-1 Diphenylacetaldehyde 
• 98-88-4 benzoyl chloride 
• 15951-99-2 meso-1,2-dichloro-1,2-diphenylethane 

Downstream Products

• 645-49-8 cis-stilben 
• 588-59-0 stilbene 
• 3947-92-0 1-deutero-cis-1,2-diphenylethylene 
• 35684-26-5 (E)-(ethene-1,2-diyl-1-d)dibenzene 
• 501-65-5 diphenyl acetylene 

Relevant academic research and scientific papers

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis

Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.

A Chlorinating Reagent Yields Vinyl Chlorides with High Regioselectivity under Heterogeneous Gold Catalysis

A novel chlorinating reagent with a high concentration of HCl has enabled the highly regioselective hydrochlorination of unactivated alkynes using a commercial nanogold catalyst. No overchlorination or hydration products were formed, and various functional groups were tolerated. This hydrochlorination method could be conducted under open air.

Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides

An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido RuIV species as a key intermediate of the reaction.

Rhodium-catalyzed reaction of aroyl chlorides with alkynes

Aroyl chlorides react with terminal alkynes accompanied by decarbonylation in the presence of a catalytic amount of [RhCl(cod)]2 and PPh3 to give the corresponding vinyl chloride derivatives regioand stereoselectively in good yields.

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.

Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes.The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ.Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a.On extended treatment (E)-4a underwent subsequent iaomerization to the thermodynamically more stable Z isomer.Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions.In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution.In contrast with solution-phase hydroiodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer.E ->/- Z equilibration of the alkenyl halides 4 was shown to involve, at last in part, addition-elimination via the gem-dihalides 13.Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation.Surface-mediated addition of HBr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c.Treatment of the terminal alkynes 17 and 22 with (COBr)2 over alumina gave the dibromides 20 and 24/25, respectively, whereas use of acetyl bromide as the HBr precursor afforded the alkenyl bromides 18b and 23.

STEREOCHEMISTRY OF THE MEERWEIN REACTION. CHLOROARYLATION OF PHENYLACETYLENE

The reaction of phenylacetylene with arenediazonium chlorides in the presence of ferrous chloride or cupric chloride and also with arenediazonium tetrachlorocuprates takes place stereoselectively as trans-addition of chlorine and the aryl radical at the t