— 190 — 



not homogeneous 1 ), because a good deal of m-xylene is formed as a 

 bye-product. No free hydrogen is formed; this being probably con- 

 sumed in the reduction of the dimethyl-cyclohexadiene to dimethyl- 

 cyclohexane. As Wallach himself is engaged in further research on 

 this subject, Crossley and Renouf content themselves with communicat- 

 ing the results of their unfinished experiments. 



Upon oxidising the hydrocarbons with 4°/ aqueous solution of 

 permanganate of potassium they obtained m-xylene (b. p. 136 to 139 ; 

 b. p. of the trinitro compound 18 2°), zwphthalic acid (m. p. of the 

 methyl ester 64 to 65 ), a volatile acid (probably acetic acid), and 

 aketonicacid. Oxidation with permanganate of potassium in acetone 

 solution resulted in a body C 8 H 16 2 melting at 90 and probably 

 representing the glycol mentioned by Wallach (loc. cit.) as well as of 

 another neutral product with a low m. p., which was not further exa- 

 mined. Besides these, the investigators obtained a ketone or ketonic 

 acid. The corresponding semicarbazone melted at 129 to 131 , but 

 the molten substance only became quite clear at 182 . 



Crossley and Renouf conclude from their investigations that the 

 hydrocarbon which is formed from methyl-heptenone by abstracting 

 water contains considerable proportions of m-xylene and dimethyl-cyclo- 

 hexane, and probably not more than 30 to 4O°/ of dimethyl-cyclo- 

 hexadiene. 



Carvone. As is well known, three carvoximes (d-, 1- and i-oxime) 

 have been prepared, and these may be obtained from the carvones 

 by the action of hydroxylamine and from limonene nitroso-chlorides 

 by the splitting off hydrochloric acid. Deussen 2 ) has recently ob- 

 tained a new carvoxime in the course of converting d-limonene nitroso- 

 chloride into 1- carvoxime by acting upon it with one molecule of 

 sodium methylate. The oil which was formed in this process was 

 freed from carvoxime crystals, distilled in vacuo and analysed. The 

 analytical values agreed for an oxime C 10 H 14 :NOH. As the rotation 

 was changeable, Deussen supposed that, in addition to 1-carvoxime, 

 there was present an as yet unknown dextrorotatory oxime. As a 

 matter of fact, it was possible to separate the oximes by conversion 

 into the benzoyl-compound, the benzoyl-compound of 1-carvoxime in 

 cold ligroin being less soluble than that of the new oxime. Recrystal- 

 lised from dilute alcohol, the new benzoyl carvoxime showed the follow- 

 ing constants: m. p. 77 , [<*] D -f- 75,3° (in benzene). The new d-carv- 

 oxime recovered from the benzoyl-compound, after having been 



*) Compare Wallach: Terpene und Campher, p. 351, Leipzig, Veit & Co. 1909. 

 2 ) Zeitschr. f. Riech- und Geschmackstoffe 1 (1909), 25; through Chem. Zen- 

 tralbl. 1909, I. 1237. 



