i6S 



THE A L UMNl JOURNAL. 



(* Washington State, Walla Walla,) ranks 

 low in Table IV. 



Patagonian wheat and Black Sea, 

 Azima, Russia, class with the American 

 samples of high density. 



The rest of all the Indian and Russian 

 wheats occupy a medium position in 

 Table IV. Special mention is due per- 

 haps to the Ghirkas (Spring wheats) for 

 their comparative superiority of station 

 within the table ; they are also cleaner 

 than the Azimas (Winter wheats). Also 

 Entre Rios, South America, deserves our 

 attention. More detailed conclusions 

 are to be found appended to Table IV. 

 (Abstracted). 



Hydrocymenes and Derivatives. — E. Kremers 

 (3d Report of the Amer. Pharm. Asso., on Men- 

 thol and substances derived therefrom), from 

 his experiments concludes that the nitrosyl 

 chloride addition product of menthene has the 

 structure 



CH, CH, 



CH 



CH 



H,C 



H.X 



CH,, or 

 CHNO 



H.,C 

 H,,C 



CH.. 

 C=NOH 



CCl 



C3H, 



CCl 



CH. 



The formation of the ketone CjoH^gO, of 

 menthone CmHisO and of menthol Ci„HibOH 

 the corresponding secondary alcohol, leave no 

 doubt as to the position of the nitroso (or oxi- 

 mido) group, and consequently as to the posi- 

 tion of the chlorine atom. Whether the group 

 NO immediately rearranges itself with the hy- 

 drogen into the group = NOH or only in the 

 formation of the nitrosomenthene, is still an 

 open question. 



Wallach considers that whenever the group 

 NO is added to a carbon atom connected with a 

 hydrogen atom, a rearrangement into the 

 group ^= NOH takes place. Thiele has re- 

 cently obtained a uitroschloride from tetra- 



methylethylene h'c^*^ ~ ^*^Ch'- "^^^^ 

 is blue in color. In this compound there must 

 be present a true nitroso group NO, since no 

 hydrogen atom is present with which it can re- 

 arrange itself into the isonitroso group = NOH. 

 Baever considers the formation of a blue 



nitrosochloride from terpinolene as a proof of a 

 double linkage in this compound like this ; 



C 



O 



C 



H3C 



CH. 



Recently Tilden and Forster have shown 

 that a number of 50-called nitrosochlorides are 

 oximido derivatives. They call attention to the 

 fact that a blue color appears to be character- 

 istic of true mononitrosocompounds and con- 

 sider that the blue color produced by the action 

 of nitrosychloride or of nitrous acid upon un- 

 saturated bodies is probably due to the forma- 

 tion of a nitroso compound as a first step in the 

 process. 



The assumption of an oximido group in the 

 menthene uitroschloride may therefore not be 

 out of place until its presence has been dis- 

 proved. 



TTpon dehydration the alcohol may be ex- 

 pected to yield a terpene (terpadiene) in this 



manner: 



CH3 CH, 



CH 



CH 



HC I iCH.. 

 HC L 'CHOH 



C 



C,H, 



-H.,0= 



H.Xr llCH 

 HCL JJCH 



c 



C3H, 



It is this formula which Baeyer assigns to 

 the synthetic terpene (terpadiene) obtained by 

 him from methylisopropylchinit. The same 

 hydrocarbon might be expected by splitting off 

 hydrobromic acid from menthene dibromide. 

 A terpene has been obtained in this manner by 

 Berkenheim. Experiments undertaken in this 

 laboratory have yielded a terpene CjoH^e in the 

 same manner. Its odor reminds one strongly 

 of that of phellandrene, and upon treatment 

 with nitrous acid yielded a very small quantity 

 of a nitrosite, showing at first a melting point 

 of 87°, but after repeated precipitation from a 

 chloroformic solution by means of ether, it 

 melted at 115-116°. Berkenheim describes his 

 compound as having a limonene odor, and was 

 unable to obtain a crystalline addition product. 



Whether this hydrocarbon is a mixture of 

 two or more terpenes, future experiments must 

 decide. The yield of nitrosite is so very small 

 that a homogeneous compound can hardly be 

 expected. 



If the dehydration of the alcohol CjoHj,0 

 proves successful, a comparison of the hydro- 

 carbon obtained with that from menthene di- 

 bromide will be made. (Abstract.) 



