57754-01-5

Usage

Physical state

Clear, colorless liquid

Functional group

Trimethylsilyl group attached to the methyl carbon

Use as a protecting group

Commonly used in organic synthesis to protect alcohols during chemical reactions, allowing for selective manipulation of functional groups and preventing unwanted reactions

Use as a reagent

Utilized in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Upstream product

• 71435-93-3 o-<(trimethylsilyl)methyl>benzoic acid 
• 89-95-2 2-methyl-benzyl alcohol 
• 529-20-4 2-methylphenyl aldehyde 
• 83781-92-4 o-[(trimethylsilyl)methyl]benzyl trimethylsilyl ether 

Downstream Products

• 81522-28-3 o-<(trimethylsilyl)methyl>benzaldehyde 
• 83781-93-5 o-((trimethylsilyl)methyl)benzyl chloride 
• 104330-78-1 2-(trimethylsilylmethyl)benzyl bromide 
• 240802-24-8 C₁₇H₂₂SSi 
• 857802-75-6 (2SR,3SR)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene 
• 29422-13-7 2-phenyltetralin 
• 34599-77-4 (E)-1-methyl-2-(penta-2,4-dien-2-yl)benzene 
• 82902-64-5 (E)-1-(but-2-en-2-yl)-2-methylbenzene 
• 134261-82-8 1-Methyl-2-(1-methylene-but-3-enyl)-benzene 
• 82902-62-3 2-(2-methylphenyl)but-1-ene 
• 83845-46-9 1-Methyl-2-(1-methylene-hex-5-enyl)-benzene 
• 160929-85-1 Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-silane 
• 160929-86-2 {2-[1-Ethyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-trimethyl-silane 

Relevant academic research and scientific papers

Electrochemical generation and reaction of o-quinodimethanes from {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]-methyl]thio} benzenes

(equation presented) The anodic oxidation of {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.

Synthesis and Conversions of Substituted o-[(Trimethylsilyl)methyl]benzyl p-Tolyl Sulfones to o-Quinodimethanes and Products Thereof

Use of o-[(trimethylsilyl)methyl]benzyl p-tolyl sulfone (3) for synthesis and cycloaddition of substituted o-quinodimethanes has been investigated. Sulfone 3 is prepared from 2-methylbenzyl alcohol (4) by reactions with n-BuLi and chlorotrimethylsilane to form o-[(trimethylsilyl)methyl]-benzyl alcohol (7) which phosphorus tribromide converts to o-[(trimethylsilyl)methyl]benzyl bromide (8). Displacement of 8 with sodium p-toluenesulfinate yields 3. Sulfone 3 is alkylated at its α-sulfonyl position upon deprotonation with n-BuLi followed by methyl iodide, ethyl, butyl, allyl, and benzyl bromides, and 5-bromo-1-pentene, respectively. Acylations occur using acid chlorides. Dialkylation occurs upon further reaction with n-BuLi and an alkyl halide. 1,4-Eliminations of α,α-dialkyl sulfones 11 with tetrabutylammonium fluoride (TBAF) give α,α-dialkyl-o-quinodimethanes (29); 3 is therefore a synthon for the o-quinodimethane-α,α-dianion (34). o-Quinodimethanes 29 undergo (1) cycloaddition with acrylonitrile, acrylate esters, and alkyl fumarates to yield 1,1-disubstituted-tetrahydronaphthalenes (30) and (2) 1,5-sigmatropic rear-rangements of hydrogen to give styrenes (32). The stereochemistries of the various cycloadditions reveal significant mechanism information.

DIRADICAL CYCLIZATION METHODOLOGIES. MODEL STUDIES PROBING THE APPLICATION OF PHOTOINDUCED-ELECTRON TRANSFER PROCESSES IN SYNTHETIC ROUTES TO THE PROTOBERBERINE AND SPIROBENZYL ISOQUINOLINE ALKALOIDS

Model studies have demonstrated that diradical cyclization processes, promoted by excited state electron transfer-desilylation pathways, serve as novel methods for construction of ring systems found in members of the protoberberine and spirobenzyl isoquin