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 oxy naphthalene, 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 hydroxyl for hydrogen, especially when the formation of a 

 derivative in the para-position is possible (KLINGENBERG). For example,' 

 aniline, Cells. NH2, passes into paraminophenol, which latter passes into 

 the urine as its ethereal-sulphuric acid, H^N.CeH^O.SC^.OH (F. MULLER).' 

 Acetanilid is in part converted into acetyl paraminophenol (JAFFE and 

 HILBERT, K. MORNER), and carbazol into oxycarbazol (KLINGENBERG) ? 



An oxidation of the side chain may occur by the hydrogen atoms being 

 replaced by hydroxyl, or may also take place with the formation of carboxyl; 

 thus, for example, toluene, CeHs.CHs (SCHULTZEN and NAUNYN), ethyl- 

 benzene, CeHs^Hs, and propylbenzene, CeH^CaHr (NENCKI and GiAco&A) 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^CHs^, is oxidized 

 into toluic acid, C6H4(CH 3 )COOH (SCHULTZEN and NAUNYN); mesitylene, 

 C 6 H 3 (CH 3 )3, into mesitylenic acid, C 6 H 3 (CH 3 )2.COOH (L. NENCKI); 

 cymene, (CH 3 ) 2 CH.C 6 H 4 .CH 3 , into cumic acid, (CH 3 )CH.C6H 4 .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. Miiller, Deutsch. med. Wochenschr., 

 1887; Jaffe and Hilbert, Zeitschr. f. physiol. Chem., 12; Morner, ibid., 13; Klingen- 

 berg, " Studien iiber 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. Jacob sen, ibid., 12. 



