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Nitration of phenylpropiolic acid derivatives in HSO3F and reactions of vinyl type cations formed therefrom.
- Source :
-
Russian Journal of Organic Chemistry . Nov2004, Vol. 40 Issue 11, p1633-1637. 5p. - Publication Year :
- 2004
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10704280
- Volume :
- 40
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Russian Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16904092
- Full Text :
- https://doi.org/10.1007/s11178-005-0070-9