Synthetic Utilization of Polynitroaromatic Compounds. 1. S-Derivatization of 1-Substituted 2,4,6-Trinitrobenzenes with Thiols

Authors:
  • GKG. Kislitsin
    G. Kislitsin
  • VSV. Samet
    V. Samet
  • ASA. Serebryakov
    A. Serebryakov
  • DKD. Konyushkin
    D. Konyushkin
  • VSV. V. Semenov
    V. V. Semenov
  • AIA. C. Buchanan Iii
    A. C. Buchanan Iii
  • AGA. A. Gakh
    A. A. Gakh
Publisher website
Google Scholar
Abstract
Reactions of 1-R-2,4,6-trinitrobenenes (R = alkyl, protected aldehyde, aminocarbonyl, cyano groups, or isoxazole ring) with thiol salts were investigated. In most cases, these reactions gave a mixture of minor para and major ortho substitution products. Reactions of N,N-disubstituted 2,4,6-trinitrobenzamides with S-,O-, and N-nucleophiles afforded products of substitution of the p-nitro group exclusively. 1-Cyano-2,4,6-trinitrobenzene was found to be the most reactive and the least selective: all three nitro groups can be substituted using an excess of thiol salts. 2-R-4,6-dinitrobenzamides showed no regioselectivity under similar conditions to yield 1:1 mixtures of para and ortho isomers.

This publication has 13 references indexed in Scilit: