20152-01-6

Upstream product

• 917-64-6 methyl magnesium iodide 
• 20518-12-1 2-methoxy-2-phenyl-1,2,3,4-tetrahydro-benzo[c]siline 
• 127208-91-7 C₁₆H₁₈Si 
• 127208-88-2 (2-Diazomethyl-benzyl)-dimethyl-phenyl-silane 
• 6231-40-9 benzyl(vinyl)dichlorosilane 
• 20151-72-8 2,2-dimethoxy-1,2,3,4-tetrahydro-benzo[c]siline 
• 6231-39-6 1,2,3,4-tetrahydro-2,2-dichloro-2-silanaphthalene 

Relevant academic research and scientific papers

Reactivity of functionalized arylcarbenes. 2-Phenylethyl side chains and hetero analogues

Phenylcarbenes with -X-CH2Ph and -CH2-X-Ph (X = CH2, O, SiMe2) groups in the ortho position were generated thermally and photolytically from diazo or tosylhydrazone precursors. Stereorandom insertion reactions with β-C-H bonds were observed, pointing to a triplet abstraction-recombination mechanism. Large kinetic and stereochemical deuterium isotope effects support this notion. The ample formation of benzocyclobutenes from 2-CH2-X-Ph substrates is due to insertion of the carbenes into ArCH2-X bonds. Addition to the terminal phenyl groups competes with C-H and C-X insertion. The results of benzophenone sensitization and of trapping with methanol suggest that the intramolecular reactions of functionalized arylcarbenes proceed, at best, competitively with spin inversion.