C(OH)CO>H H 2 C 



CH 2 H 2 C 



C-CH 8 



CNH 2 



or 



H 2 C 



H 2 C 



C-CH, 



C:NH 



CH 2 



CCHa 



VI 



VII 



VIII 



Carvone. As in the case of limonene (see p. 138), G. Vavon 1 ) has 

 observed several phases when reducing d-carvone with platinum and 

 hydrogen. Jn this case also, observation of the rotation indicates the 

 extent to which the process of reduction has progressed and it is there- 

 fore possible readily to isolate the various reduction-products. The first 

 reduction-product obtained by Vavon was d-carvotan acetone: b. p. 227 

 to 228°, d~ 0,937, |V| 578 + 59,8°, n D20O 1,4817. Further progress of the 

 reduction led to tetrahydrocarvone : b. p. 218 to 219°, d^ 0,904, [a] 57 8 — 27°, 

 n D 2oo 1,4555. Finally, Vavon obtained carvomenthol: b. p. 217 to 218°, 

 d~ 0,908, [«] 578 — 24,7°, n D20O 1,4648. The acetate of carvomenthol is a 

 liquid with a pleasant odour, b. p. 230 to 231° (d^ 0,928; [a] 518 — 27,6°; 

 "d2oo 1,4477); the benzoate possesses the following constants: b. p. 185 

 to 186° (15 mm.), d 2 -g 1,006, H 57 8 - 12,9°, n D20 o 1,509. 



Vavon has not only reduced carvone, but a whole series of other 

 ketones and aldehydes into their corresponding alcohols by means of 

 hydrogen in the presence of platinum. The substances so treated include 

 acetone, methylethylketone, benzophenone, ci/c/ohexanone, valeric aldehyde, 

 cenanthol, benzaldehyde, vanillin, piperonal, and anisic aldehyde. 



Phenols and Phenolethers. 



A. Angeli, L. Alessandri and R. Pegna' 2 ) are engaged on research 

 into the action of nitroso derivatives, and especially of nitroso benzene, 

 upon unsaturated compounds. Like dihydroxyammonia NH(OH) 2 , nitroso- 

 benzene C 6 H 5 NO, the phenyl ether of anhydrous dihydroxy ammonia H- NO, 

 reacts upon double bonds. In this capacity nitrosobenzene was tested 

 for its behaviour towards certain allyl and propenyl compounds. It was 

 found to dissolve only slowly in anethol and in ^sosafrol (both propenyl 

 derivatives), forming a brown liquid from which no characteristic bodies 

 were obtainable. Combinations with allyl groups, as for example safrol and 

 eugenol ethyl ether, afforded well-defined reaction-products. Safrol reacted 



!) Compt. rend. 153 (1911), 68. 



2 ) Rendiconti della R. Accad. dei Lincei Vol. 19, Ser. 5, 1 st Half-year, no. 10, p. 650. Meeting 

 of 22 nd May, 1911. From a reprint kindly sent to us. 



