— I3i — 



upon the combinations in question. By splitting -up with water the 

 ozonides which are formed it is found that the propenyl compounds 

 yield the corresponding aldehydes (isosafrol, for instance, yielding 

 piperonal), whereas allyl compounds give the corresponding homologous 

 combinations. For example: safrol yielded, besides homopiperonylic 

 acid, a considerable proportion of homopiperonal possessing the follow- 

 ing properties: m. p. 69 , b. p. 143 to 144 under 10 mm. pressure, 

 d2o° i> 2 95> n D 1,571 1 7, mol. refr. found 41,67, calculated 41,69. 

 The semicarbazone melted at 189 , the oxime (b. p. 180 to 181 at 

 10 mm. pressure; m. p. 124 to 125 ) yielded upon boiling with acetic 

 anhydride homopiperonylic acid nitrile (b. p. 153 to 156 at 10 mm. 

 pressure; d2o° 1*231; n D 1,53698) from which by saponification homo- 

 piperonylic acid, C 9 H 8 4 (m. p. 127 ), was obtained. The methyl ester 

 (b. p. 153 to 1 55 at 10 mm. pressure; d2o° 1,246; n D 1,534; mol. refr. 

 47,73, calculated 47,98) when reduced with sodium in alcoholic solution, 

 yielded homopiperonyl alcohol C 9 H 10 O 3 (b. p. 156 at 10 mm. press. 

 n D * ,54 7 80) with an odour reminding of ylang-ylang. When the 

 nitrile referred to above was reduced, a base C 9 H 11 2 N (b. p. 146 

 to 148 at 10 mm. press; d2(p 1,225; n D 1,5620) was formed of which 

 the picrate melted at 160 . 



Lsevulic aldehyde. Laevulic aldehyde obtained by action of ozone 

 upon unsaturated compounds such as allylacetone, methyl heptenone, 

 2,6 -dimethyl heptadiene-2,5, citral, geraniol, linalooi, caoutchouc, 

 and gutta percha has been more closely examined by C. Harries 

 and M. Boegemann 1 ). We will only briefly mention here that a 

 series of experiments pointed to the probability of the compound 

 possessing the formula CH 3 • CO • CH 2 • CH 2 • CHO, but in a few cases 

 it behaved abnormally, which was probably due to steric conditions. 



Ketones. 



Sabina ketone. In continuation of previous syntheses carried 

 out by means of sabina ketone, O. Wallach 2 ) has now prepared some 

 symmetrical di-isopropyl derivatives. He condensed sabina ketone with 

 isopropyl magnesium iodide, and by decomposing the resulting product, 

 he obtained an alcohol with an odour reminding of terpineol, and a 

 b. p. of 102 to 107 at 14 mm. pressure. When shaken with dilute 

 sulphuric acid this alcohol was slowly converted into the corresponding 

 terpine : 



(CH 3 \CH-C(OH)/ \C(0H)-CH(CH 3 ) 2 . 



*) Berl. Berichte 42 (1909), 439. 



2 ) Liebig's Annalen 362 (1908), 283. 



