32047-17-9

Upstream product

• 501-65-5 diphenyl acetylene 
• 151416-94-3 (Z)-2,2'-[1,2-(biphenyl)eth-1-ene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 64-17-5 ethanol 
• 40788-61-2 1-amino-4,5-diphenyl-1,2,3-triazole 
• 861078-14-0 α,α,α'-tribromo-bibenzyl 
• 14541-26-5 bromo(phenyl)carbene 
• 829-85-6 diphenylphosphane 
• 65567-06-8 lithium diphenylphosphide 
• 2592-73-6 1,1-dibromo-2,2-diphenylethylene 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 
• 2489-03-4 tribromomethylbenzene 
• 4541-89-3 2-chloro-1,1-diphenylethene 
• 108-88-3 toluene 
• 15219-34-8 Oxalyl bromide 

Downstream Products

• 501-65-5 diphenyl acetylene 
• 882-33-7 diphenyldisulfane 
• 134-81-6 benzil 
• 5088-12-0 acetic acid-(α'-bromo-stilben-α-yl ester) 
• 1707-03-5 diphenyl-phosphinic acid 
• 14447-39-3 cis-1,2-diphenylvinyldiphenylphosphine oxide 
• 603-32-7 triphenyl-arsane 
• 2741-42-6 benzyl diphenyl arsine 
• 573-34-2 2,4,5-triphenyloxazole 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 14447-39-3 (E)-(1,2-diphenylethenyl)diphenylphosphane oxide 
• 1212-08-4 S-Phenyl benzenethiosulfonate 

Relevant academic research and scientific papers

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide

Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.

Mild oxidative bromination of alkenes and alkynes with zinc bromide and lead tetraacetate

Zinc bromide and lead tetraacetate is a practical and safe source of bromine. The combined reagents are used to brominate a variety of alkenes to vicinal dibromoalkanes. Similarly, alkynes can be converted into dibromoalkenes in high yields. The reagents are also capable of tetrabromination of alkynes.

Spin selectivity in the oxygenation of singlet phenylhalocarbenes with oxygen

Singlet phenylhalocarbenes are shown to react with triplet oxygen and the apparent spin-forbidden oxygenation rates are strongly dependent on substituents, i.e. in the decreasing order of Br>Cl?F for halogen and of p-NO2>H?p-MeO for p-substituents. These results suggest the oxygenation of triplet halocarbene equilibrated with ground-state singlet, resulting in the first estimation of energy difference between the singlet and triplet states.

Spectroscopic and theoretical investigations of electrophilic bromination reactions of alkynes: The first evidence for π complexes as reaction intermediates

A bromine-alkyne π complex (λmax = 294 nm) of 1:1 stoichiometry has been observed for the first time in the course of the bromination of 1-phenylpropyne by means of a diode-array stopped-flow technique. The formation enthalpy and entropy (ΔHsu

Palladium(0) complex-catalyzed debrominative coupling of (tribromomethyl)- and (dibromomethyl)benzenes to diarylacetylenes and 1,2-diarylethenes

Palladium(0)-triphenylphosphine complex-catalyzed debrominative coupling reaction of (tribromomethyl)benzenes gave diarylacetylenes or a mixture of (E)- and (Z)-α,β-dibromostilbenes depending upon the substrate and the solvent being used. On the other hand, (dibromomethyl)benzenes afforded (E)-stilbenes selectively under the same reaction conditions.

Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with N-Bromosuccinimide

Tri- and dibromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide were accomplished by photothermal reaction with a tungsten lamp in carbon tetrachloride or benzene. (Dibromomethyl)arenes and (tribromomethyl) derivatives were produced depending upon a solvent used and a substituent on the benzene ring.In the bromination of methylbenzenes without a substituent on the ortho-position, (tribromomethyl)benzenes were formed.On the other hand, ortho-substituted methylbenzenes gave (dibromomethyl)benzenes. α,β-Dibromo-1,2-diarylstilbenes were formed via the debrominative carbon-carbon coupling reaction of ...

A New Synthetic Method of Preparing Iodohydrin and Bromohydrin Derivatives through in Situ Generation of Hypohalous Acids from H5IO6 and NaBrO3 in the Presence of NaHSO3

Hypohydrous acids such as hypoiodous acid (IOH) and hypobromous acid (BrOH) were found to be easily generated from H5IO6 and NaBrO3 in the presence of an appropriate reducing agent such as NaHSO3.Iodohydrin and bromohydrin derivatives were synthesized in good yields from the reaction of a wide variety of organic compounds bearing carbon-carbon double bonds, with H5IO6 or NaBrO3 and NaHSO3.The iodohydroxylation of internal alkenes was achieved with high stereoselectivity to give anti products, although no stereoselectivity was observed in the bromohydroxylation of these alkenes.It was found that allylic alcohols undergo iodohydroxylation in anti-Markovnikov fashion to form iodo diols in good yields.Treatment of alkynes with H5IO6 combined with NaHSO3 afforded the corresponding ketones in fair yields, but the same treatment with NaBrO3 rather than H5IO6 produced the corresponding α,α-dibromo ketones along with small amounts of the dibromoalkenes.

THE BROMINATION OF METHYLARENES WITH NBS BY IRRADIATION USING A TUNGSTEN LAMP. PREPARATION OF BENZOTRIBROMIDES

Bromination of toluene and its meta- and para-substituted derivatives with NBS by irradiation using a tungsten lamp gave benzotribromides and cis- and trans-1,2-dibromo-1,2-diaryl-ethylenes, while ortho-substituted toluenes gave benzal bromides. o-Xylene gave tetra- and pentabromides and m-xylene afforded a mixture of dibromodiarylethylenes.

Phosphides and Arsenides as Metal-Halogen Exchange Reagents. Part 1. Dehalogenation of Aliphatic Dihalides

Lithium diphenylphosphide and arsenide have been investigated as reagents for metal-halogen exchange.Reactions involving two molar equivalents of the anions with 1,2-dibromoethylenes lead to moderate to good yields of acetylenes and smaller yields of phosphorus-containing by-products.Similar reactions with 2,3-dichlorobuta-1,3-diene and 2-chlorobuta-1,3-diene give SN2' rather than direct substitution products.Evidence is presented that adamantene is an initial product in the reaction of lithium diphenylphosphide with 1,2-di-iodo- and 1,2-dibromo-adamantane, but not with 1,2-dichloroadamantane, although 1- and 2-adamantyldiphenylphosphine oxides are formed in every case.Finally reactions of phosphide anion with geminal dihalides were briefly investigated; 1,1-dibromo-2,2-diphenylethylene gave diphenylacetylene as the major product.