108459-81-0

Upstream product

• 13361-64-3 trimethyl(propargyl)silane 
• 100-52-7 benzaldehyde 
• 76943-59-4 (E)-3-trimethylsilyl-1-chloro-1-propene 

Downstream Products

• 111999-89-4 1-(trimethylsilyl)-4-phenyl-4-methoxy-2-butyne 
• 108459-89-8 (4-Trimethylsilanyl-1-trimethylsilanyloxy-but-2-ynyl)-benzene 

Relevant academic research and scientific papers

A REGIOSELECTIVE SYNTHESIS OF 2-TRIBUTYLSTANNYL-1,3-DIENES

Hydrostannylation of 1-trimethylsilyl-4-hydroxy-2-alkyne derivatives followed by acetylation of the OH group and fluoride ion-catalysed 1,4 elimination of the silyl and the acetate groups afforded 2-stannyl-1,3-dienes with high regio- and stereoselectivit

Cobalt-catalyzed mono-coupling of R3SiCH2MgCl with 1,2-dihalogenoethylene: A general route to γ-substituted (E)-allylsilanes

The reaction of trimethylsilylmethylmagnesium chloride (TMSCH 2MgCl) with 1,2-dihalogenoethylene in the presence of 1mol% of Co(II) or Co(III) acetylacetonate in THF or THF-NMP proceeded exclusively in a mono-coupling pathway to provide 3-trimethylsilyl-1-halogeno-1-propene with >99% of E geometry in high yield, which was converted to a variety of γ-substituted allylsilanes by Ni- or Pd-catalyzed coupling with organometallic compounds.

STANNYLDIENES, NEW TOOLS FOR ORGANIC SYNTHESIS. PREPARATION AND REACTIVITY.

Tributylstannyl-1,3-dienes could be considered synthetic equivalents of conjugated dienic anions.The preparation of differently substituted 2- and 3-trialkylstannyl-1,3-dienes is reported starting from propargyltrimethylsilane.The position of the stannyl moiety on the dienic skeleton can be controlled by hydrostannylation of (trimethylsilyl)propargyl alcohols or stannyl cupration of (trimetylsilyl)propargyl ketones.The so obtained stannyldienes are submitted to Diels Alder reaction and the corresponding cycloadducts functionalized through the C-Sn bond.Stannyldienes are also suitable for a regiocontrolled transfer of the dienic structure by : a) tin-lithium exchange and further reaction with aldehydes to give conjugated dienic alcohols; b)coupling with acyl chlorides in the presence of palladium catalysts to give conjugated dienic ketones; c) AlCl3 promoted reaction with acyl chlorides to give allenic ketones.

Some Observations on the Stereochemical and Regiochemical Outcome of Hydrostannylation of Substituted Propargyl Alcohols

A regio- and stereocontrolled hydrostanyllation of substituted propargyl alcohols and derivatives has been performed.Tri-n-butylstannyl hydride reacts with different substituted propargyl alcohols to give a mixture of Z/E isomers of vinylstannane with the stannyl moiety bonded to the carbon closest to the OH or OR group.A careful study of the reaction conditions allowed the preparation and isolation of pure Z isomer for a wide set of compounds.The reaction products are unstable under the conditions of preparation.An outline of the possible mechanism of the reaction is described.

SYNTHESE D'HETEROCYCLES OXYGENES A GROUPE VINYLIDENE EXOCYCLIQUE PAR VOIE ORGANOSILICIQUE - PARTIE II*: PREPARATION DE VINYLIDENE-5 DIOXANNES-1,3

The α-silyloxypropargyltrimethylsilanes regiospecifically react with aliphatic aldehydes to lead to alkyl-substituted 5-vinylidene-1,3-dioxanes, in a one-pot reaction.