76-63-1

Usage

Uses

Used in Chemical Synthesis:
Allyltriphenyltin is used as an allylating reagent for the C-H phenylation of azoles, which is catalyzed by palladium. This application is crucial in the synthesis of complex organic molecules and contributes to the development of novel chemical compounds with potential applications in various industries.
Used in Alkylidene Meldrum's Acids Allylation:
In the alkylidene Meldrum's acids allylation, catalyzed by Sc(OTf)3, allyltriphenyltin plays a vital role as an allylating reagent. This process is essential for the synthesis of various organic compounds, including those with potential pharmaceutical or industrial applications.
Used in Total Synthesis of Antifungal Molecules:
Allyltriphenyltin is employed as a reagent in the total synthesis of (+)-ambruticin S, an antifungal molecule. This application highlights the compound's importance in the development of new antifungal agents, which are crucial for treating various fungal infections.
Used in Insect Chemosterilants:
Allyltriphenyltin is also utilized as an insect chemosterilant, playing a significant role in pest control and management. By disrupting the reproductive capabilities of insects, ALLYLTRIPHENYLTIN contributes to the development of environmentally friendly and sustainable pest control strategies.

Hazard

A poison.

InChI:InChI=1/3C6H5.C3H5.Sn/c3*1-2-4-6-5-3-1;1-3-2;/h3*1-5H;3H,1-2H2;/rC21H20Sn/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h2-17H,1,18H2

Upstream product

• 639-58-7 triphenyltin chloride 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 1793-90-4 allyltriethylgermane 
• 7646-78-8 tin(IV) chloride 
• 4167-90-2 lithium triphenylstannide 
• 107-05-1 3-chloroprop-1-ene 
• 463-49-0 1,2-propanediene 
• 892-20-6 triphenylstannane 
• 89958-47-4 Mo(C₅H₅)(CO)(NO)(CH₂CHCH₂Sn(C₆H₅)3) 

Downstream Products

• 2114-42-3 allylcyclohexane 
• 64198-20-5 3-cyclohexylbutyronitrile 
• 73970-92-0 1-(prop-enyl)-4-phenyl-1,2,4-triazolidine-3,5-dione 
• 111874-57-8 1-methoxy-4-(1-methoxybut-3-en-1-yl)benzene 
• 134311-00-5 4-(4-methoxyphenyl)-4-(4-methoxyphenyl)-1-butane 
• 134310-99-9 4-(4-methoxyphenyl)-4-(4-methylphenyl)-1-butene 
• 17180-49-3 2-methyl-1-phenylpent-4-en-1-one 
• 54848-79-2 allyl(2-(nitrophenyl))sulfane 
• 3112-87-6 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 

Relevant academic research and scientific papers

Nucleophilicity vs basicity in the reaction of sodium tert-butoxide with β-stannyl ketones

The reaction of 3-stannyl-1,2,3-triphenyl- and 3-stannyl-1,3-diphenyl-2-methylpropanones with sodium tert-butoxide in either t-BuOH or dimethyl sulfoxide (DMSO) as solvent leads to elimination and/or substitution products. The composition of the product m

Wurtz-type reductive coupling reaction of allyl bromides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to allylstannanes and hexaaryldistannanes

Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (Bu2SnCl)2O in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = α-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (α-isomer), and (ii) the subsequent isomerization of the α-isomer furnishing mixtures of (α, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the α-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br?-Zn?+ radical ion which is trapped by the R3SnCl reactant to form the α-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl?-Zn?+ radical ions with R3SnCl molecules.

The effect of ligands, solvent and temperature on the reactions of allyltin(IV) compounds with singlet oxygen

The reaction of singlet oxygen with a variety of allyltin compounds CH2=CHCH2SnR3 (R3 = Me3, Bu3, allyl3, (cyclo-C6H11)3, Ph3, allylBu2, Bu2Cl, Bu2OAc, allylCl2, allylCl2bipy) has been investigated, and the allylperoxytin compounds, 3-stannylallyl hydroperoxides, and 4-stannyl-1,2-dioxolanes which result from M-ene, H-ene and cycloaddition processes, respectively, have been identified by NMR spectroscopy.As the tin centre becomes more electropositive, as indicated by the 13C NMR shift of the allylic CH2 group, the proportion of the M-ene reaction increases, and when δCH2 is above about 23.7, the allylperoxytin compound is the only product.An exception to this rule is tetraallyltin, δCH2 16.13, which similarly shows only the M-ene reaction.This is tentatively ascribed to the special effect of hyperconjugation between the C-Sn ?-bond and the remaining ?-systems.A polar solvent favours the M-ene reaction.The cycloaddition reaction is favoured by low temperature, and at -70 deg C in a non-polar solvent it may become the major route.Diallylmercury and allylmercury chloride react with singlet oxygen to show only the M-ene reaction, but also undergo extensive photosensitized decomposition.With 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), allylmercury chloride shows only the M-ene reaction.

Hydrostannation and Hydrogermylation of Allenes

Treatment of allenes with Ph3SnH or Ph3GeH in the presence of Pd(PPh3)4 catalyst provides the corresponding allylic stannanes or allylic germanes in good yields.Et3B induced radical addition of Ph3SnH or Ph3GeH to allenes are also described.

Transition-metal complexes corresponding to the insertion into a group 4B element-carbon bond. 3. Reactivity of complexes with unsaturated carbon-carbon bonds. Crystal structure of (η5-cyclopentadienyl)(triphenylgermyl) (η3-hexenyl) nitrosylmolybdenum

Anions of the type [(η5-C5H5)(CO)(L)(M4BPh 3)MT]- (L = CO, NO; M4B - Si, Ge, Sn; MT = Mn, Mo, W) react with allyl halides, affording neutral σ-bonded alkenyl derivatives. These new complexes can rearrange to η3-allyl complexes and also lose (allyl)M4B to give η2-allyl complexes. According to the nature of both the transition metal and the group 4B metal η1, η3, or η2 complexes are obtained. A mechanism for these successive reactions is proposed. Butenyl and hexenyl iodides also react with the anions, affording η1 complexes that can eliminate CO and rearrange to a η3 ligand as shown by X-ray structure determination.