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OXIDATION IN THE NUCLEUS AND SIDE CHAIN. 779
readily destroyed than the corresponding meta- and para-compounds.
The claims of Juvalta and Porcher are unfortunately disputed by
Pribram and Pohl.1
An oxidation in the side chain of aromatic compounds is often found,
and may also occur in the nucleus itself. As an example, benzene is first
oxidized to oxybenzene (Schultzen and Naunyn), and this is then
further in part oxidized into dioxybenzenes (Baumann and Preusse).
Naphthalene appears to be converted into oxynaphthalene, and probably
a part also into dioxynaphthalene (Lesnik and M. Nencki). The hydro-
carbon with an amino- or imino-group may also be oxidized by a sub-
stitution of hydroxy! for hydrogen, especially when the formation of a
derivative in the para-position is possible (Klingenberg). For example,
aniline, C6H5.NH2, passes into paraminophenol, which latter passes into
the urine as its ethereal-sulphuric acid, H2N.C6H4.O.SO2.OH (F. Muller).
Acetanilid is in part converted into acetyl paraminophenol (Jaffe and
Hilbert, K. Morner), and carbazol into oxycarbazol (Klingenberg).2
An oxidation of the side chain may occur by the hydrogen atoms being
replaced by hydroxy), or may also take place with the formation of carboxyl;
thus, for example, toluene, C6H5.CH3 (Schultzen and Naunyn), ethyl-
benzene, CGH5.C2H5, and propylbenzene, C6H5.C3H7 (Nencki and Giacosa)3
besides many other bodies, are oxidized into benzoic acid. Cymene is
oxidized to cumic acid, xylene to toluic acid, methylpyridine to pyridine-
carboxylic acid in the same way.
If several side chains are present in the benzene nucleus, then only one
is always oxidized into carboxyl. Thus xylene, CeH^CHV^, is oxidized
into toluic acid, CeH^CH^OOOH (Schultzen and Naunyn); mesitylene,
C6H3 (CH3)3, into mesitylenic acid, C6H3 (CH3)2.COOH (L. Nencki);
cymene, (CH3)2CH.C6H4.CH3 , into cumic acid, (CH3 )CH.C6 H4 .COOH
(M. Nencki and Ziegler 4
).
If the side-chain has several members, then the behavior is dif-
ferent and in these cases the demolition of aromatic amino-acids and
fatty acids is especially to be considered.
1
Juvalta, Zeitschr. f. physiol. Chem., 13; Pribram, Arch. f. exp. Path. u. Pharm.,
51; Porcher, Bioch. Zeitschr., 14; Pohl, ibid., 16.
2
Schultzen and Naunyn, Arch. f. (Anat. u.) Physiol., 1867; Baumann and Preusse,
Zeitschr. f. physiol. Chem., 3, 156. See also Nencki and Giacosa, ibid., 4; Lesnik and
Nencki, Arch. f. exp. Path. u. Pharm., 24; F. Muller, Deutsch. med. Wochenschr.,
1887; Jaffe and Hilbert, Zeitschr. f. physiol. Chem., 12; Morner, ibid., 13; Klingen-
berg, " Studien liber die Oxydation aromatischer Substanzen," etc., Inaug.-Diss.,
Rostock, 1891.
3
Zeitschr. f. physiol. Chem., 4.
4
Nencki, Arch. f. exp. Path. u. Pharm., 1; Nencki and Ziegler, Ber. d. d. Chem.
Gesellsch.. 5; see also O. Jacobsen, ibid., 12.
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