80278-99-5

Upstream product

• 3839-31-4 dimethyl(phenyl)silyllithium 
• 75-56-9 methyloxirane 
• 108-86-1 bromobenzene 
• 768-33-2 phenyldimethylsilyl chloride 
• 693-02-7 hex-1-yne 
• 1833-51-8 chloromethyldimethylphenylsilane 
• 75-07-0 acetaldehyde 
• 18001-18-8 allyldimethylphenylsilane 

Downstream Products

• 1252913-71-5 1-(dimethylphenylsilyl)-2-propyl 3,5-dinitrobenzoate 
• 1252913-70-4 1-(dimethylphenylsilyl)-2-propyl trifluoroacetate 
• 15527-42-1 (2-ethoxypropyl)dimethylphenylsilane 
• 1252913-99-7 C₁₃H₁₇⁽²⁾H₅OSi 

Relevant academic research and scientific papers

The β-silicon effect. 4: Substituent effects on the solvolysis of 1-alkyl-2-(aryldimethylsilyl)ethyl trifluoroacetates

Solvolysis rates of 2-(aryldimethylsilyl)-1-methylethyl and 2-(aryldimethylsilyl)-1-tert-butylethyl trifluoroacetates were determined conductimetrically in 60% (v/v) aqueous ethanol. The effects of aryl substituents at the silicon atom on the solvolysis rates at 50 °C were correlated with σmacr; parameters of r+ = 0.15 with the Yukawa-Tsuno equation, giving ρ values of-1.5 for both secondary α-Me and α-tert-Bu systems. The ρ values for those secondary systems are less negative than-1.75 for the 2-(aryldimethylsilyl)ethyl system that proceeds by the Eaborn (non-vertical) mechanism, while they are distinctly more negative than-0.99 for 2-(aryldimethylsilyl)-1-phenylethyl system that should proceed by the Lambert (vertical) mechanism. There was a fairly linear relationship between the reaction constants (ρ) for the β-silyl substituent effects and the solvolysis reactivities for a series of β-silyl substrates. The solvolyses of the α-Me and tert-Bu substrates proceed through the transition state (TS) with an appreciable degree of the β-silyl participation, close to the Eaborn (non-vertical) TS rather than to the Lambert (vertical) TS. Copyright

The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes

The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron

REGIOCHEMISTRY IN THE HYDROBORATION OF ALLYLSILANES

The hydroboration of most types of allylsilane is highly selective for the formation of the product having the silicon and boron in a 1,3 relationship when the hydroborating agent is 9-BBN.There is only a low degree of correlation between the difference in the chemical shifts of the trigonal carbon atoms on an alkene and the regioselectivity in hydroboration with either borane:THF or 9-BBN.

The Silylcupration of Acetylenes: a Synthesis of Vinylsilanes

Bis(dimethylphenylsilyl)copper-lithium (1) reacts with hex-1-yne, propyne, acetylene itself, phenylacetylene, and hex-3-yne to give the products of syn addition of the dimethylphenylsilyl group and the copper.The resultant vinylcopper reagents react with a variety of electrophiles, such as the proton, iodine, acyl and alkyl halides, enones, and epoxides, to give vinylsilanes.With the terminal alkynes, the silyl group becomes attached with a high level of regioselectivity to the terminal carbon atom, with the result that the final products are 2,2-disubstituted vinylsilanes.