21453-89-4

Upstream product

• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 19647-26-8 (Z)-β-bromo-α-methylstyrene 
• 16917-35-4 (E)-(1-bromoprop-1-en-2-yl)benzene 
• 4962-45-2 2-bromo-1-phenyl-propan-1-ol 
• 100-42-5 styrene 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 2048-31-9 (Z)-2-bromo-3-phenylprop-2-en-1-ol 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 23970-90-3 (Z)-(2,3-dibromoprop-1-en-1-yl)benzene 
• 536-74-3 phenylacetylene 
• 71-43-2 benzene 
• 17497-85-7 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 124582-43-0 (Z)-tributyl(1-phenylprop-1-en-2-yl)stannane 
• 78338-60-0 trimethyl<(Z)-1-phenylprop-1-en-2-yl>stannane 
• 122245-43-6 C₁₂H₁₂N₂ 
• 673-32-5 1-Phenylprop-1-yne 
• 2327-99-3 1-phenylpropadiene 

Relevant academic research and scientific papers

Regiochemical variation in the electrophilic addition of HBr to 1-phenylprop-1-yne

The reaction of aryl alkynes with dilute methylene chloride solutions of quaternary ammonium bromide and 20% trifluoroacetic acid produces primarily the syn Markovnikov adducts of hydrogen bromide. At moderate concentrations of the bromide, the principal

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

Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex

Hydrodebromination of allylic and benzylic bromides was successfully achieved by a rhodium porphyrin complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.

Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

A green hunsdiecker reaction of cinnamic acids

Tribromo- and trichloroisocyanuric acids react with cinnamic acids in NaOH/H2O/Et2O at room temperature to produce (E)-2-halostyrenes regioselectively in 25-95percent yield. Mechanism studies using Hammett correlations and DFT (density functional theory) calculations have shown that this reaction has as rate determining step the electrophilic addition of chlorine atom to the double bond.

Convergent and stereoselective synthesis of trisubstituted E-alkenyl bromides and iodides via β-oxido phosphonium ylides

β-Oxido phosphonium ylides, generated in situ from aldehydes and Wittig reagents [alkylidene(triphenyl)phosphoranes, other than ethylidene(triphenyl)phosphorane], react readily with electrophilic halogen sources to form predominantly or exclusively E-brom

Photochemical generation of highly destabilized vinyl cations: The effects of α- and β-trifluoromethyl versus α- and β-methyl substituents

(Chemical Equation Presented). The photochemical reactions in methanol of the vinylic halides 1-4, halostyrenes with a methyl or a trifluoromethyl substituent at the α- or β-position, have been investigated quantitatively. Next to E/Z isomerization, the reactions are formation of vinyl radicals, leading to reductive dehalogenation products, and formation of vinyl cations, leading to elimination, nucleophilic substitution, and rearrangement products. The vinyl cations are parts of tight ion pairs with halide as the counterion. The elimination products are the result of β-proton loss from the primarily generated α-CH3 and α-CF3 vinyl cations, or from the α-CH3 vinyl cation formed from the β-CH3 vinyl cation via a 1,2-phenyl shift. The β-CF 3 vinyl cation reacts with methanol yielding nucleophilic substitution products, no migration of the phenyl ring producing the α-CF3 vinyl cation occurs. The α-CF3 vinyl cation, which is the most destabilized vinyl cation generated thus far, gives a 1,2-fluorine shift in competition with proton loss. The experimentally derived order of stabilization of the vinyl cations photogenerated in this study, α-CF3 3 3 3, is corroborated by quantum chemical calculations, provided the effect of solvent is taken into account.

Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes

(Chemical Equation Presented) The first examples of Lewis acid catalyzed hydrogermylation of alkynes have been demonstrated. It was found that this method has much higher functional group compatibility compared to the known Lewis acid catalyzed hydrosilyl

The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity

In a weakly acidic solution, the addition of HBr to 1-phenylprop-1-yne produces predominantly the anti-Markovnikov product. In this paper, we consider five possible explanations for this behavior and conclude that the concerted addition is occurring on the acetylenic π bond orthogonal to the extended aromatic π system. The electronic effect of the distal methyl group and the steric hindrance of the coplanar phenyl ring combine to promote bromide attack at the β carbon. Attack on this π bond is insensitive to the electronic effect of meta and para substituents on the ring but is very (sterically) sensitive toward all ortho substituents.

Halodecarboxylation of a,β-unsaturated carboxylic acids bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide

Reaction of α,β-unsaturated carboxylic acid bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide in aqueous acetonitrile afforded the corresponding haloalkenes.