7506-76-5

Upstream product

• 24850-33-7 allyltributylstanane 
• 106-95-6 allyl bromide 
• 249626-07-1 (R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one 
• 1160850-10-1 1,3-dichloro-2-propyl 2-chlorobenzoate 
• 609-65-4 o-chlorobenzoyl chloride 
• 107-18-6 allyl alcohol 
• 5831-77-6 2-allyloxypyridine 
• 118-91-2 ortho-chlorobenzoic acid 
• 99893-62-6 2-chlorobenzoic acid propargyl ester 

Downstream Products

• 1344667-73-7 2-allyl-6-chlorobenzoic acid 
• 1372715-48-4 1-methoxy-1-oxo-2-phenylpent-4-en-2-yl 2-chlorobenzoate 
• 1384266-32-3 (Z)-prop-1-enyl 2-chlorobenzoate 
• 1384266-31-2 (E)-prop-1-enyl 2-chlorobenzoate 
• 1558039-91-0 C₁₀H₁₁ClO₄ 
• 1558039-92-1 allyl (5S,6R)-5,6-dihydroxy-2-chlorocyclohexa-1,3-dienecarboxylate 

Relevant academic research and scientific papers

Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes

A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.

In situ synthesis of 2-allyloxy-1-methylpyridinium triflate for the allylation of carboxylic acids

2-Allyloxypyridinium triflate is formed in situ by treating a mixture of 2-allyloxypyridine, a carboxylic acid, and toluene with methyl triflate. Subsequent warming of the reaction mixture in the presence of potassium carbonate leads to efficient formation of allyl esters in good to excellent yields.

[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters

The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.

Palladium-catalyzed divergent reactions of α-diazocarbonyl compounds with allylic esters: Construction of quaternary carbon centers

Take two: α-Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium-catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different C-C bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O-substituted quaternary carbon center. Copyright

Rhenium-catalyzed allylation of C-H bonds of benzoic and acrylic acids

We have succeeded in the allylation of aromatic and olefinic C-H bonds of benzoic and acrylic acids using a rhenium catalyst, Re2(CO) 10. In this reaction, isomerization of the introduced allyl group to the 1-propenyl group did not occur.

A tandem Finkelstein-rearrangement-elimination reaction: a straightforward synthetic route to allyl esters

Allyl esters can be obtained by a Finkelstein-rearrangement-elimination reaction of 2-chloro-1-(chloromethyl)ethyl esters induced by NaI. Sodium iodide can be used below equivalence using a reductive agent as sodium thiosulfate. High yields are obtained with most of the diverse esters studied. The method described avoids the use of allyl alcohol as a reagent. 2-Chloro-1-(chloromethyl)ethyl esters are prepared from glycerol, the main by-product of biodiesel industry. The effectiveness of iodine as reagent to hydrolyze allyl esters is also confirmed.

A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and α,β-unsaturated δ-valero lactones

The synthesis of arylated dihydropyrans and unsaturated lactones starting from enantiomerically pure α-hydroxy ketones (prepared by an enzyme-catalyzed benzoin condensation) is described. The key steps are a highly diastereoselective addition of vinyl metal compounds under chelate control and a ruthenium-catalyzed ring-closing olefin metathesis reaction. Elucidation of the relative configuration of the final products was achieved by NOE experiments.

THE SYNTHESIS, CHARACTERISATION AND REACTIVITY OF SOME LEAD(IV) CARBOXYLATES

A detailed examination of the preparation, characterisation and reactivity of a range of lead(IV) carboxylates is reported.The replacement of the acetate ligands of lead(IV) tetraacetate by other carboxylates gives the lead(IV) tetracarboxylates 1-16, which have usually been found to be more stable than lead tetraacetate with respect to hydrolysis.These compounds react with allyltributylstannane to give high yields of the corresponding allyl esters 20-34 under mild conditions.