160929-84-0

Basic information

• Product Name: Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane
• Synonyms: Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane
• CAS NO: 160929-84-0
• Molecular Weight: 360.593
• Mol File: 160929-84-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane(160929-84-0)
• EPA Substance Registry System: Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane(160929-84-0)

Safety Data

• Hazardous Substances Data: 160929-84-0(Hazardous Substances Data)

Upstream product

• 155203-56-8 Trimethyl-[2-(toluene-4-sulfonylmethyl)-benzyl]-silane 
• 74-88-4 methyl iodide 
• 160929-76-0 Trimethyl-{2-[1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane 

Downstream Products

• 7399-49-7 1-methyl-2-(prop-1-en-2-yl)benzene 
• 160929-91-9 1,2,3,4-tetrahydro-1,1-dimethyl-2-naphthonitrile 
• 66042-29-3 o-dimethylquinodimethane 
• 23203-56-7 4,4-Dimethyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 

Relevant articles and documents

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.