72486-22-7

Upstream product

• 18255-05-5 benzyl phenyl selenide 
• 870-63-3 prenyl bromide 
• 7310-74-9 triphenylcinnamylphosphonium bromide 
• 67-64-1 acetone 
• 134792-05-5 2-((E)-3-Phenyl-prop-2-ene-1-sulfonyl)-benzothiazole 
• 20279-29-2 phenyl isobutyrate 
• 104-55-2 3-phenyl-propenal 
• 27644-03-7 4-methyl-1-phenyl-pent-3-en-1-ol 
• 90-02-8 salicylaldehyde 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-42-5 styrene 
• 103-64-0 bromostyrene 
• 17137-22-3 (E)-4-Methyl-1-phenyl-pent-1-en-3-ol 

Downstream Products

• 81238-63-3 3,3-dimethyl-6-phenyl-1,2-dioxa-4-cyclohexene 
• 81238-70-2 (E)-4-hydroxy-4-methyl-1-phenyl-2-penten-1-one 

Relevant academic research and scientific papers

Synthesis of Furo[3,2-c]benzopyrans via an Intramolecular [4 + 2] Cycloaddition Reaction of o-Quinonemethides

An intramolecular [4 + 2] cycloaddition reaction of o-quinonemethides generated from salicylaldehydes and α-prenylated alcohols is described. In the presence of a catalytic amount of benzenesulfonic acid (BSA), the reaction proceeded smoothly in EtOH to afford furo[3,2-c]benzopyrans through a three-bond forming process in moderate to excellent yields with high diastereoselectivity. This reaction provides a simple and straightforward protocol to efficiently construct furo[3,2-c]benzopyran skeletons. A possible mechanism involving hemiacetal formation/hetero-Diels-Alder reaction is proposed to rationalize the observed results.

On the antibiotic activity of oxazolomycin

Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of β-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents.

Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis

A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.

Cyclialkylation of arylalkyl epoxides with solid acid catalysts

Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Bronsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.

Regioselective palladium-catalysed coupling reactions of vinyl chlorides with carbon nucleophiles

Vinyl chlorides bearing methyl groups in the 2-position can be activated catalytically by palladium(0)-complexes of 1,4-bis(dicyclohexylphosphino)butane, the process involving vinyl-allyl isomerization via CH-activation followed by nucleophilic attack of

A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2'-alkenyl)- or benzyl-sulfonyl]-benzothiazoles

During the title reaction, the lithium alkoxides formed as intermediates undergo an intramolecular addition to the neighboring C = N group followed an S to O benzothiazole transfer and simultaneous extrusion of sulfur dioxide and ejection of 2(3H)-benzothiazolone anion.

PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.

An improved variant of the Julia olefin synthesis: Reductive elimination of β-hydroxy imidazolyl sulfones by samarium diiodide

The reductive elimination reaction of β-hydroxy imidazolyl sulfones 1 to afford the corresponding olefins can be accomplished under mild conditions and in good yields using SmI2, offering a convenient modification of the Julia olefin synthesis.

An E-Selective 1,3-Diene Synthesis from Moderated Ylides and Aldehydes

The synthesis of E-1,3-dienes by the Wittig reaction of aldehydes and ylides is described.

Anwendungen der Phasentransfer-Katalyse 18. Horner-Emmons Reaktionen

Optimale Bedingungen fuer die Darstellung von Olefinen aus den relativ wenig aktivierten Benzyl-, Cinnamyl- und Crotonylphosphonestern wurden aufgesucht.Als Carbonylkomponenten koennen aromatische Aldehyde und (mit verminderten Ausbeuten) auch aliphatische Aldehyde und Ketone eingesetzt werden.Die beste Basen-Loesungsmittel-Katalysator-Kombination ist Benzol/gepulvertes KOH/18-Krone-6.Im Gegensatz zur phasentransfer-Katalytischen Wittig-Reaktion wird die Ausbeute bei der Horner-Reaktion durch die Gegenwart des Kronenethers verbessert.Mechanistische Schlussfolgerungen aus diesem Befund werden diskutiert.