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benzole and alcohol solutions, was found t o be t h e mofit serviceable for effecting the separation of t h e constituents of the product under examination. Upon decomposing t h e picric acid compounds, t h u s separated, they obtained a t least t w o distinct hydrocarbons, one fusing at 280' C., the other a t 178' C. T h e quinones of these compounds were prepared, and from t h e hydrocarbon fuRing at 280' C . , the alizarine was alfio obtained, analyses of which indicate that this hydrocarbon has the composition C,,H,,, and is a dimethyl-anthracene, although not identical with the dimethyl-anthracene of V a n Dorp. The other hydrocarbon is apparently monomethyl-anthracene. T h e authors are at present engaged in the study of this subject, and defer fnrther discussion thereof until the completion of the same. 0 t h the Oxidation of Substitution Products of Aromatdc Wydrocnrbons, b y Prof. IRAREMsm.-The author, in a report of a former investigation on para-sulphobenzoic acid, * referring t o the oxidation products of ortho and para-tolnenesulphonic acids and sulphamides, expressed the opinion that the ortho compounds are lesg easily oxidized than t h e para compounds. His view was corroborated upon treating a mixture of the two isomeric sulphonic acids with an oxidizing agent (chromic acid), and fusing the product obtained with potassium hydrate, when salicylic acid, but no ortho-sulphobenzoic acid waR formed ; also, on separately treating t h e potassium salts of the t w o sulphotoluenic acids with an oxidizing agent under similar conditions ; and on submitting t h e t w o toluene-sulphamides t o t h e same process. H e is led b y these results t o the enquiry, whether t h e influence of a substituting group in the ortho position is such as to prevent t h e conversion of the hydrocarbon residue into carboxyl, and notes the investigations of Beilstein and Kreusler t on t h e oxidation of nitroxylene (by which monobaRic nitro-toluic acid is formed), as indicating t h a t the action of the chromic acid is limited t o a single methyl group ; and t h e experiments of Vollrath, 1 showing t h a t para-chlorxylene behaves like the analogous nitro-derivative. T h e researches of Fittig, Ahrens and Mattheides 8 on bromxylene are also mentioned as affording similar results, and it is remarked that t h e entrance of a substituting group into xylene greatly affects its behavior towards chromic acid, one of the methyl group being protected ~
"Amer. Jour. Sci., vol. v., 179, 274, 854. Ann. der Chem., 178, 275. t Ann. der Chem., 144, 168. $Ibid, 144, 266. $ Ibid, 147, 32.
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against oxidation, the other remaining at least comparatively unaffected. I n regard to the position occupied 11) the protecting group. t h e author's experiments with the sulpho derivativeb of toluene indicate that the protected methyl group ocwpies the ortho positioii F i t t i g * states that all ortho cornpoiiitds arc. c~ompleteljdecsompoaed on treatment with chromic acid, and remarks that the experimcntc of Beilstein likewise show that the ortho sribqtitution producth of toluol a r e affected in the same manner, u-hicli aoiild indicate that ortho compounds are ZPM stable than those of the other seriw, R view which is of no assistance in the explanation of the i7icreri~;dstability of these compouiids. T h e author regards as very probable the conclusion " that in all cases now on record, in which hydrocarbon residue8 are shown to be protected from oxidation 1)) the preseilcr of negative gi'oups, the latter are in the ortho position with reference to the former; whereas, oxidizable residues, situated either iii the meta or para position with reference t o the negative groups, are, under the Rame circumstances, transformed, just as if the iiegati\ e groups u era not present," and proceeds to describe the investigationh which lead hini t o this opinion. On the OcidatJon of .XUlercerruLphnmidee, by IRAREVSEN and M. W. ILEs.--In this unfinished communication, which is a notice of t h e investigations upon which the deductions mentioned in the preeeeding article are based, the authors describe the preparation of the sulphamides of xylene, and the oxidation products obtained therefrom. T h e xylene was first converted into sulphonic acids, and the corresponding amides were then prepared. Of these, three distinct modifieations were obtained, t h o of which were divided from metaxylene, t h e third from paraxylene. T h e former, which are designated as a n d /r xylenesulphamides, fuse respectively a t 137' and 97' ; t h e latt e r at 143'. Ori several occasions a compound corresponding to ortho-xylenesulphamide was was also obtained. r p o n oxidation, the amide is converted into a monobasic acid, fusing at 247.5'; the fi amide giving under the same circumstances very small quantities of an acid which was not further examined. T h e acid obtained from t h e amide has the compositioii C,H,SNO,, and is derived from the amide b y the oxidation of one of the methyl g r o u p , CH, T h e acid is C,H, ;%€I T h e amide being C,H, CH, ( SO,NH, SO,", and, as the amide is derived from metaxylene, the acid which would be formed from it by the oxidation of one methyl group, would be
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