30262-96-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 30263-02-6 1-Phenyl-1-trimethylsilyl-3-butanol 
• 937-53-1 (Z)-4-phenylbut-3-en-2-one 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 917-54-4 methyllithium 
• 107486-95-3 (E)-3-phenyl-1-trimethylsilyl-2-propen-1-one 
• 4360-47-8 cinnamonitrile 
• 56919-90-5 (E)-4-(trimethylsilyl)but-3-en-2-ol 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 5930-98-3 4-trimethylsilyl-3-butyn-2-one 
• 1896-62-4 (E)-benzalacetone 
• 49750-09-6 (E)-1-trimethylsilyl-1-buten-3-one 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Downstream Products

• 30263-02-6 1-Phenyl-1-trimethylsilyl-3-butanol 
• 79239-10-4 2-methyl-4-phenyl-4-trimethylsilylbutan-2-ol 
• 15325-61-8 3-methyl-1-phenyl-1-butene 
• 15325-61-8 (E)-(3-methylbut-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Stereoselective synthesis of 1,2,3-triol derivatives from α,β-unsaturated acylsilanes

The stereoselective synthesis of 1,2,3- triol derivatives having contiguous stereogenic centers from α,β-unsaturated acylsilanes 1 was described. The oxidation of an olefin moiety of 1 with osmium tetroxide proceeded smoothly to give the corresponding 2,3- syn-dihydroxyacylsilanes 2. The protection of two hydroxy groups of 2 followed by a nucleophilic reaction to the silyl carbonyl group gave the corresponding silylated triol derivatives (7 and 8) with high stereoselectivity, depending on the kind of nucleophilic reagents. The deprotection for 7 and 8 and the following protodesilylation gave two isomers of possible four 1,2,3- triol derivatives. The stereoselective triol synthesis by asymmetric diolization of α-silylated allyl alcohols 11 derived by nucleophilic addition to 1 was also investigated.

Palladium/Me3SiOTf-catalyzed bis-silylation of α,β-unsaturated carbonyl compounds without involving oxidative addition of disilane

In the presence of a catalytic amount of Me3SiOTf and palladium(0), the addition of disilane to α,β-unsaturated carbonyl compounds proceeds under very mild conditions via η3-siloxyallylpalladium generated by the reaction of enone, en

Synthesis of β-silylated olefins from α,β-unsaturated aldehydes and ketones

α,β-Unsaturated aldehydes and ketones such as phorone, benzalacetone, benzalacetophenone, 4-(2-furyl)-3-buten-4-one and β-ionone, react with TMS-Cl in the presence of Li in THF to give conjugated β-silylated enoxysilanes. Hydrolysis of this compounds in a

Electroreductive silylation of activated olefins using a reactive metal anode

Electroreductive silylation of α, β-unsaturated esters, nitriles and ketones in the presence of Me3SiCl using a reactive metal anode (Mg, Zn, Al) in an undivided cell afforded the corresponding β-silyl compounds offering a valuable method for introduction of a silyl group into activated olefins.

Catalytic asymmetric synthesis of β-hydroxy ketones by palladium-catalyzed asymmetric 1,4-disilylation of α,β-unsaturated ketones

1,4-Disilylation of β,β-unsaturated ketones with 1,1-dichloro-1-phenyl-2,2,2-trimethyldisilane proceeded in the presence of phosphine-palladium catalysts in benzene. High enantio-selectivity (up to 92%) was observed in the disilylation with dichloro[(R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] palladium(II) as a catalyst (0.5 mol %). The disilylation products, 1-(trimethyisilyloxy)-3-(dichlorophenylsilyl)propenes, were readily converted into optically active α-unsubstituted or anti α-substituted β-(phenyldimethylsilyl) ketones, the oxidation of which gave the corresponding optically active β-hydroxy ketones in high yields.

Barium Permanganate, Ba(MnO4)2, a versatile and mild oxidizing agent for use under aprotic and non-aqueous conditions

Barium Permanganate is an easily prepared, stable, and a versatile oxidation reagent. With this reagent different types of primary and secondary hydroxy compounds are converted to their carbonyl derivatives. Aldehydes could be transformed to their carboxylic acids. Benzylic chloride and bromides are converted to their aldehydes and carboxylic acids. Semicarbazide and 2,4-dinitrophenylhydrazine derivatives of benzylic carbonyl compounds undergo carbon-nitrogen bond cleavage selectively and yield the expected carbonyl compounds. p-Hydroquinone is converted to p-benzoguinone and aromatic amines to their azo compounds. Anthracene and phenanthrene produce their 9,10-quinones. Diphenyl acetylene and trans stilbene give benzil, and styrene produces benzaldehyde. Selective oxidations of secondary benzylic carbon-hydrogen bonds occur and the corres- ponding carbonyl compounds are produced in good yields.

EVIDENCE FOR A REVERSIBLE d,?*-COMPLEXATION, β-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION REACTION OF GILMAN REAGENTS WITH α,β-ENONES.

In situ trapping of reaction intermediates combined with stereochemical studies of the reaction of lithium dimethylcuprate with enones provides evidence for a pathway involving d,?*-cuprate-enone and copper(III) β-adducts as important intermediates in cuprate-mediated conjugate addition of carbon.

Some uses of silicon compounds in organic synthesis

1.The amount of γ-phenylthioalkylation of silyl dienol ethers is increased when the triphenylsilyl ether is used in place of the trimethylsilyl ether.Phenylthiomethylation is the least γ-selective carbon electrophile of several tried so far. 2.The acid-catalysed reactions of a range of γ-silyl tertiary alcohols cleanly give rearrangement, in which the silyl group controls the outcome.The reactions are similar in several respects to the rearrangements of the corresponding pinacols, except that the silicon controlled reactions are usually cleaner and give higher yields.The reaction is particularly useful for setting up quaternary carbon atoms.

THE SYNTHESIS OF αβ-UNSATURATED KETONES FROM β-SILYLENONES AND β-SILYLYNONES

Conjugate addition, followed by alkylation, bromination and desilyl-bromination make the β-silylketone (4) an a3d2-synthon (5) and the β-silylynone (6) a 2a3d2-synthon (7).