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

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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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Authors and Affiliations

  1. St. Petersburg State Academy of Forestry Engineering, 194021, St. Petersburg, Russia

    P. Yu. Savechenkov, A. P. Rudenko & A. V. Vasil’ev

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  1. P. Yu. Savechenkov
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  2. A. P. Rudenko
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  3. A. V. Vasil’ev
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Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1665–1677.

Original Russian Text Copyright © 2004 by Savechenkov, Rudenko, Vasil’ev.

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Savechenkov, P.Y., Rudenko, A.P. & Vasil’ev, A.V. Nitration of phenylpropiolic acid derivatives in HSO3F and reactions of vinyl type cations formed therefrom. Russ J Org Chem 40, 1633–1637 (2004). https://doi.org/10.1007/s11178-005-0070-9

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  • DOI: https://doi.org/10.1007/s11178-005-0070-9

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