Abstract
Nitration of phenylpropiolic acid derivatives ArC≡CX (X=CN, CO2Me) in HSO3F at −75...−50°C afforded mononitro compounds, for instance, m-O2NC6H4C≡CX. Vinyl type cations generated in HSO3F from methyl 3-arylpropiolates ArC+=CHCO2Me react along two pathways. The first among them results in formation of fluorosulfonates ArC(OSO2F)=CHCO2Me, and the second one after the attack of vinyl cation on the aryl moiety of the substrate affords a dimer that on nitration is converted into a nitro product with conserved triple bond.
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