108415-97-0

Upstream product

• 3418-21-1 2-(bromomethyl)-2-phenyl-1,3-dioxolane 
• 108-86-1 bromobenzene 
• 764-48-7 ethyleneglycol vinyl ether 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 98-86-2 acetophenone 
• 108415-83-4 (E)-β-styryl phenyl selenone 
• 146791-31-3 1-<2-<(trimethylsilyl)oxy>ethoxy>-1-phenylethene 
• 108415-91-4 1-phenyl,1-(2-hydroxy)ethoxy,2-phenylselenonylethane 

Downstream Products

• 153632-95-2 <1-(2-n-Butoxyethoxy)ethenyl>benzene 
• 98-86-2 acetophenone 
• 1408078-60-3 2-(1-phenylvinyloxy)ethyl benzoate 

Relevant academic research and scientific papers

Cyclopentyl methyl ether-NH4X: A novel solvent/catalyst system for low impact acetalization reactions

Cyclopentyl methyl ether, a low impact ether forming a positive azeotrope with water, was successfully employed as a solvent in the synthesis of 1,3-dioxanes and 1,3-dioxolanes carried out under Dean-Stark conditions by the acetalization of aliphatic and aromatic aldehydes or ketones, employing ammonium salts as environmentally friendly acidic catalysts.

Optimization of Grignard ring-opening of α-brominated dioxolanes for the preparation of β-hydroxy-protected vinyl ethers by a three-step one-pot procedure

Aliphatic, cyclic, and aromatic benzoate-protected γ-hydroxy enol ethers were prepared from α-brominated dioxolanes by a three-step reaction procedure and a one-pot protocol involving Grignard reagent formation, ring-opening, and final benzoate protection

Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water

(Chemical Equation Presented) Highly regioselective and fast Pd(0)-catalyzed internal α-arylation of ethylene glycol vinyl ether with aryl halides was shown to be possible in water without the need for any halide scavengers or ionic liquid additives. This presents, to our knowledge, the first case of water being utilized in the selective arylation of electron-rich olefins. Resulting α-products were hydrolyzed and isolated as corresponding acetophenones in good to excellent yields when using aryl bromides and with good to moderate yields in the case of aryl iodides. Microwave irradiation was shown to be beneficial in activation of aryl chlorides toward the internal Heck arylation. The scope of the protocol was further increased to include different hydroxyalkyl vinyl ethers, these all giving selectively only branched α-products. Finally, the active role of the hydroxy group in directing the regioselectivity toward internal arylation of electron-rich olefins, even in nonpolar toluene, was revealed.

Facile synthesis of enol ethers by cleavage of α-bromoacetals and α-bromoketals mediated by SmI2

α-Bromocyclicacetals, α-bromocyclicketals and α-bromocyclicthioketals, derived from cyclic and acyclic ketones and aldehydes, reacted with samarium diiodide at -78°C in THF to furnish the corresponding enol ethers or thioenol ethers containing hydroxy or thiol moieties in high yields.

FORMATION AND REACTIVITY OF THE ADDITION PRODUCTS OF ALKOXIDES AND THIOLATE ANIONS TO VINYL SELENONES

Vinyl selenones react with sodium methanethiolate in methanol to give the product of conjugate addition and subsequent displacement of the selenonyl group.On the contrary, the same reaction carried out with alkoxide anions affords the conjugate addition products in excellent yields.These β-alkoxy alkyl phenyl selenones are stable compounds which can react in several ways with loss of the selenonyl group.Their reactions with MeONa or MeSNa have been investigated both in MeOH and in DMF.The products observed derive from substitution and elimination processes as well as from retro Michael reactions followed by nucleophilic substitution of the vinyl selenone thus generated.These results indicate that the ArSeO2 is a strong electron attracting group with peculiar properties.Beside making acidic the α-hydrogen atoms it activates the carbon-carbon double bond towards the addition of anionic reagents and it acts as a good leaving group in nucleophilic substitution, both aliphatic and vinylic, and in elimination reactions.The appropriate choice of the reagent and of the solvent allows to direct the reaction towards the desired products.Useful synthetic applications of these reactions are presented.