57266-92-9

Upstream product

• 30006-66-7 bis(trimethylsilyl)diazomethane 
• 100-52-7 benzaldehyde 
• 97537-99-0 (E)-2-phenyl-1-trimethylsilylethenyllithium 
• 77-78-1 dimethyl sulfate 
• 109-72-8 n-butyllithium 
• 65425-96-9 (Z)-β-bromo-β-(trimethylsilyl)styrene 
• 75-16-1 methylmagnesium bromide 
• 185844-50-2 ((Z)-1-Methanesulfonyl-2-phenyl-vinyl)-trimethyl-silane 
• 185844-37-5 Trimethyl-((Z)-1-methylsulfanyl-2-phenyl-vinyl)-silane 
• 74-88-4 methyl iodide 
• 87739-09-1 1,1-Bis(trimethylsilyl)-1-(phenylthio)ethane 
• 673-32-5 1-Phenylprop-1-yne 
• 65343-66-0 Tris(trimethylsilyl)aluminium 
• 185844-35-3 (Z)-2-phenyl-1-trimethylsilylethenenethiol 

Downstream Products

• 15174-47-7 α-methyl-trans-cinnamaldehyde 

Relevant academic research and scientific papers

The reaction of substituted vinylsilanes with lithium metal

Vinylsilanes are known to react with lithium metal to form either 1,2-dilithioethanes by reduction or 1,4-dilithiobutanes by reductive dimerization. The reaction of the substituted vinylsilanes 3, (Z)-13b, 17b, c, 42b, c, 44, and 51 with lithium has been investigated. Depending on the substituents on the vinylsilane and the solvent employed, several new reaction pathways are observed, which have been proved by independent syntheses of the reactive intermediates (E)-14b, 18d, and 25-27. Thus, besides the known elimination of lithium hydride, either a 1,4-proton shift of 25 to 26 or a Grovenstein-Zimmerman rearrangement of 45 to 47 can occur as follow-up reactions. Furthermore, two different types of dimerization of the silyl-substituted vinyllithium compounds have been identified. Either the vinyllithium compound 18d adds to the starting vinylsilane leading to the monolithiumorganic species 41, or lithium metal catalyzed dimerization to the 1,4-dilithio-2-butene derivative 49 takes place, which is without precedence.

Chemistry of silyl thioketones. Part 10. Synthesis and reactivity of α-silyl vinyl sulfldes

Aliphatic silyl thioketones containing an α-hydrogen atom undergo enethiolization to Z-α-silyl enethiols 2. Compounds 2 react with a variety of halides R3X to give open-chain α-silyl vinyl sulfides 3. Protiodesilylation of 3 was achieved upon treatment with fluoride ion to give vinyl sulfides 4. Reaction of 3 with Grignard reagents, in the presence of an appropriate nickel catalyst, results in a series of vinylsilanes 5 with a specific geometry.

STUDIES ON THE SYNTHETIC USE OF STEREODEFINED OLEFINS WITH GEMINAL TRIMETHYLSILYL AND TRIMETHYLSTANNYL SUBSTITUENTS

The synthetic use of 2-alkyl and 2-(hetero)aryl substituted (Z)- and (E)-1-trimethylsilyl-1-trimethylstannylethenes of general formula (Z)-2, (E)-2, (Z)-3 and (E)-3, via the corresponding 1-silylethenyllithiums prepared by tin-lithium exchange reactions a

FORMATION OF α-SILYLVINYLLITHIUM REAGENTS: REACTIONS OF α-SILYL- AND α-STANNYL-VINYLLITHIUMS WITH ALDEHYDES AND KETONES

The formation of α-trimethylsilylvinyllithium compounds from 1-trimethylsilyl-1-trimethylstannyl-1-alkenes have been studied and their stabilities investigated. α-Trimethylsilyl- and α-trimethylstannyl-vinyllithiums undergo 1,2-addition to aldehydes and non-enolisable ketones, to give silyl- or stannyl-substituted allylic alcohols; α,β-unsaturated ketones, however, undergo 1,4-addition to give homoallylic ketones.

SYN-ADDITION VON TRIS(TRIMETHYLSILYL)ALUMINIUM AN ALKINE: EINE NEUE SYNTHESE FUER VINYLSILANE

A new method for the synthesis of vinylsilanes by syn-addition of tris(trimethylsilyl)aluminium to alkynes is described.

Bis(trimethylsilyl)-, Trimethylsilyltrimethylgermyl-, and Bis(trimethylgermyl)diazomethane. Synthesis and Chemistry of Quantitative Silene and Germene Precursors

Convenient syntheses of bis(trimethylsilyl)diazomethane (1), trimethylsilyltrimethylgermyldiazomethane (22), and bis(trimethylgermyl)diazomethane (31), utilizing diazo transfer from tosyl azide to the carbanion derived from the corresponding bis(trimethylmetallo)methane or -chloromethane, are described.Both photolysis and thermolysis of 1 produce a carbene which rearranges via methyl migration to silene 3, which dimerizes.Trapping results with methanol, benzaldehyde, 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, and D2O indicate that silene formation is essentially quantitative.Thermolysis of 23 produces only products from silene intermediacy, but photolysis and trapping with MeOD reveal a competition between silene and germene formation which favors the silene by a factor of 4.Both photolysis and pyrolysis of 31 produce only products from the germene resulting from methyl migration to carbon.