Nitration of phenylpropiolic acid derivatives in HSO3F and reactions of vinyl type cations formed therefrom

Author： Savechenkov P.   Rudenko A.   Vasil’ev A.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.40, Iss.11, 2004-11, pp. : 1633-1637

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

Previous Menu Next

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.

Related content

Reactions of Vinyl Type Carbocations Generated in Fluorosulfonic Acid with Benzene Derivatives. New Synthesis of Alkyl 3,3-Diarylpropenoates

By Savechenkov P.   Rudenko A.   Vasil'ev A.   Fukin G.  

Russian Journal of Organic Chemistry, Vol. 41, Iss. 9, 2005-09 ,pp. : 1316-1328 (13)

MAIK Nauka/Interperiodica

Access to resources Recommend Favorite

Thermodynamic study on the sublimation of 1,2-diphenylethane and of 3-phenylpropiolic acid

By Monte M.J.S.   Hillesheim D.M.  

Journal of Chemical Thermodynamics, Vol. 33, Iss. 8, 2001-08 ,pp. : 849-857 (9)

Academic Press

Access to resources Recommend Favorite

The crystal structure of phenyl‐propiolic acid

By  

Acta Crystallographica, Vol. 8, Iss. 8, 1955-08 ,pp. : 487-494 (8)

John Wiley & Sons Inc

Access to resources Recommend Favorite

Brønsted Acid Ionic Liquid [(CH2)4SO3HMIM][HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives

By Heravi Majid   Saeedi Mina   Karimi Narges   Zakeri Masumeh   Beheshtiha Yahya   Davoodnia Abolghasem  

Synthetic Communications, Vol. 40, Iss. 4, 2010-01 ,pp. : 523-529 (7)

Taylor & Francis Ltd

Access to resources Recommend Favorite

Kinetics of 2,4-dihydro-1,2,4-triazol-3-one nitration in nitric acid

By Zhilin V.   Zbarskii V.   Yudin N.  

Kinetics and Catalysis, Vol. 47, Iss. 6, 2006-12 ,pp. : 846-849 (4)

MAIK Nauka/Interperiodica

Access to resources Recommend Favorite