Meta toluene sulphonic acid and related compoundsAllen, C. F. H. (Charles Francis Hitchcock)
Science
Meta toluene sulphonic acid and related compounds
Allen, C. F. H. (Charles Francis Hitchcock)
Organic compounds -- Synthesis; Sulfonic acids
Griffin, (Dissertation, 1895), prepared what he thought was a solution
of the meta toluene sulphonic acid from the amide, and made and studied
several salts as well as the anilide and toluide. However he did not
investigate his solution to find out what it contained, but went ahead
on the assumption that he had a solution of this acid. It is on the
basis of his lack of investigation that I am working.
The derivatives of para toluene sulphonic acid have been made and
studied by Newell, (Dissertation, 1895), and are being investigated
further. He prepared para tolyl phenyl sulphone by the Friedal-Crafts
reaction, para phenyl sulphone benzoic acid by oxidation of the
sulphone with chromic acid, its salts, chloride, amide, and anilide,
and para benzoyl diphenyl sulphone from the acid by the Friedal-Crafts
reaction, and studied their reactions and properties.
The analogous derivatives of ortho toluene sulphonic acid were made
and studied by Canter, (Dissertation, 1900). He prepared ortho tolyl
phenyl sulphone by the Friedal-Crafts reaction, ortho phenyl sulphone
benzoic acid by oxidation of the sulphone by potassium permanganate,
its chloride, amide, and anilide, and ortho benzoyl diphenyl sulphone
from the acid by the Friedal-Crafts reaction.
The analogous derivatives of the meta toluene sulphonic acid with one
or two exceptions have not been made or studied, nor has the acid
itself been prepared in a form which could be recognized. The following
derivatives of meta toluene sulphonic acid have been made and studied;
the amide by Müller, Pechmann, Pagel, Beckurts, F.H.S. Muller, Nevile
and Winther, Chase Palmer, Klason, Valin, Noyes and Walker, Metcalf,
and Griffin; meta sulphamine benzoic acid by Limpricht and Uslar,
and Griffin; meta toluene sulphon anilide and toluide by Muller and
Wiesinger, (Ber. d. chem. Ges, 12,1348), and by Griffin; the latter
also made and studied several metallic salts.
The literature on the ortho and para toluene sulphonic acids and
their derivatives is voluminous, and covers a great many derivatives
which have been thoroughly studied and whose structure has been
determined. The literature on meta toluene sulphonic acid is very
meagre, comparatively, and all that could be found is mentioned in this
paper. This would seem to indicate that investigators have avoided
this series, and apparently the reason is due to the difficulties
encountered in isolating the free acid.
THEORETICAL DISCUSSION
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