174710-87-3

Upstream product

• 5908-41-8 benzoyltrimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 13411-45-5 trimethyl(2-phenyl-1,3-dithian-2-yl)silane 
• 100-52-7 benzaldehyde 

Downstream Products

• 250236-00-1 C₁₄H₂₁⁽²⁾HOSi 

Relevant academic research and scientific papers

Methyllithium-promoted Wittig rearrangements of α-alkoxysilanes

(matrix presented) The Wittig rearrangements of α-alkoxysilanes, promoted by the action of methyllithium were studied. Depending on both the substrate and reaction conditions employed, [2,3]-, [1,2]-, or [1,4]-Wittig rearrangements can be realized. These rearrangements were shown to be initiated by either Si/Li exchange or deprotonation a to the silane. Furthermore the sigmatropic shifts can often be followed by other synthetically useful in situ chemical events.

Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride

A series of acyl silanes including aliphatic-, aromatic-, and bis-acyl silanes, as well as the acyl silanes bearing other substituents such as a bromine atom and alkenyl, succinimide, and carbonyl groups, were prepared, and their reactions with samarium diiodide or tributylstannane were studied. The reactions of acyl silanes occurred in various manners such as reductions, reductive alkylations, intramolecular radical cyclizations, pinacol couplings, aldol reactions, and Tishchenko reactions, depending on the nature of substrates and reaction conditions. Acyl silanes were generally reduced to give the corresponding α-silyl alcohols without transfer of silyl groups. Intramolecular radical cyclizations of 5-hexenoyl silanes and 1-silyl-1,5-pentanedione were realized to give α-silyl cyclopentanols and 1,2-cyclopentanediol derivatives, respectively. On treatment with samarium diiodide in tetrahydrofuran, 1-(trimethylsilyl)-1,6-hexanedione underwent a pinacol coupling reaction in the presence of t-BuOH, whereas it underwent a Tishchenko reaction in the presence of MeOH. The Tishchenko reaction of 1-silyl-1,5-pentanedione gave a δ-silyl-δ-lactone. On treating with samarium diiodide, 1-(trimethylsilyl)-1,5-hexanedione and 1,5-bis(trimethylsilyl)-1,6-hexanedione, underwent, respectively, intramolecular aldol reactions.