36004-05-4

Upstream product

• 34713-70-7 2-Phenylpropanal 
• 1826-67-1 vinyl magnesium bromide 
• 105633-12-3 [2-(Isopropoxy-dimethyl-silanyl)-ethylidene]-tris-(4-methoxy-phenyl)-λ⁵-phosphane 
• 24850-33-7 allyltributylstanane 
• 7393-43-3 tetraallyl tin 

Downstream Products

• 1431732-09-0 1-(2,6-dimethoxyphenyl)-4-phenylpentan-3-one 

Relevant academic research and scientific papers

Grignard reactions in imidazolium ionic liquids

A new, base-stable, imidazolium room-temperature ionic liquid (RTIL) has been prepared and applied to the addition of Grignard reagents to carbonyl compounds. These reactions occur readily at ambient temperature to afford the alcohol products in good to excellent yield. The RTIL can be recycled and reused numerous times without any difficulty.

The Diastereoselectivity of Electrophilic Attack on Trigonal Carbon Adjacent to a Stereogenic Centre: Diastereoselective Protonation, Epoxidation and Acylation of Allylsilanes

The four allylsilanes 6 and 8, which have a stereogenic centre carrying a phenyl group, a methyl group and a hydrogen atom adjacent to the nucleophilic end of the double bond, react with protic (or deuteronic) acid, m-chloroperbenzoic acid and chlorosulfonyl isocyanate to give eletrophilic substitution of the allylsilane, with diastereoselectivity in the sense 2, in conformity to a general rule for electrophilic attack on a double bond adjacent to a stereogenic centre.The most reliably stereoselective reactions took place with the allylsilane 6b, in which the stereogenic centre is cis to a group larger than a hydrogen atom in both the E- and Z-isomer.In general, chlorosulfonyl isocyanate induces higher stereoselectivity than the peracid, and the peracid higher stereoselectivity than the proton (or deuteron).

Fluorodestannylation. A Powerful Technique to Liberate Anions of Oxygen, Sulfur, Selenium, and Carbon

Fluoride ions smoothly destannylate organotin chalcogenides to liberate nucleophilic chalcogenide ions; hence the first nucleophilic oxide (O2-) and selenide (Se2-) transfer agents are reported where the tin atom serves as "group 16 (VIB) transfer agent".In the presence of crown ethers or ammonium salts, this process results in a new way to generate "naked" nucleophiles.Ethers and selenides are formed in good to excellent yield.In addition, a useful C-C bond-forming reaction has been developed by using alkyltins with aldehydes and acid chlorides in the presence of fluroide ion.Aspects concerning reactivity and mechanism are presented.Finally, the generality of the fluorodestannylation procedure and the differences with parallel silicon chemistry are detailed.

Syn-Diastereoselective Alkenylation with a Modified Seyferth-Wittig Reagent: Modification of the Silyl Substituents and Isopropenylation

The introduction of electronegative substituents onto the silyl group of triaryl(2-silylethylidene)phosphorane promotes eliminative silyl migration relative to the Wittig reaction; the combination of this effect with modification of the phosphorane substituents leads to highly diastereoselective reagents for alkenylation.