26167-16-8

Upstream product

• 770-09-2 benzyltrimethylsilane 
• 108-88-3 toluene 
• 98-87-3 benzylidene dichloride 
• 14595-77-8 bis(trimethylsilyl)phenylmethane 

Downstream Products

• 20124-42-9 -p-trimethylsilylbenzene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 38695-36-2 (E)-1-bromo-4-(4-fluorostyryl)benzene 
• 153227-31-7 (Z)-1-bromo-4-(4-methoxystyryl)benzene 
• 4714-24-3 (Z)-1-(4-bromophenyl)-2-phenylethylene 
• 13041-70-8 (E)-4-bromostilbene 
• 29788-02-1 p-Bis-(trimethylsilyl)-methylbenzoesaeure 

Relevant academic research and scientific papers

Stereoselective peterson olefinations from bench-stable reagents and N-phenyl imines

The synthesis of bench-stable α,α-bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ～1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N-benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as N,N-bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.