— 99 — 



they are decomposed in an explosive manner. When reduced with 

 aluminium amalgam, neither aldehydes or ketones, nor primary or 

 secondary alcohols are formed. 



Already with water they split up into aldehydes (or ketones) and 

 hydrogen peroxide, and for this reason they can only be produced in 

 absolutely dry solvents, for example chloroform. 



C-C/ + H 2 0=\C:0 + 0:C/ + H 2 2 . 



O O 



\/ 

 O 



The general behaviour of the ozonides now shows, that they can 

 be employed for the determination of the constitution of unknown 

 compounds. Thus, the action of ozone on oleinic acid and elaidinic 

 acids, supplied the exact proof of the stereo-isomerism of these tw r o 

 acids. Both acids yield ozonides of the formula C 18 H 36 6 , which, 

 when heated with water, yield the same products of decomposition, 

 viz., nonylic aldehyde (or nonylic acid) and the semi-aldehyde of 

 azelainic acid -(or azelainic acid respectively). The semi-aldehyde, 

 when exposed to the air, very rapidly combines with oxygen, and could 

 therefore not be isolated as such. 



Pulegone and pinene formed ozonides whose products of decom- 

 position are still being studied. Among others, the following ozonides 

 have also been produced: 



Methylheptenone ozonide, 



CH 3X 



> C — CH — CH 2 — CH 2 — C — CH 3 



CH 3 / \/ || 



o 3 o 



II 



o 



It is formed when methylheptenone is ozonised, as a water-white 

 syrup; d 19 o 1,1380. 



Citronellal ozonide, C 10 H 18 O 5 ; a water- white syrup, non-explosive; 

 d2i° 1,0746; when distilled in vacuo, it is split up in oxygen and 

 citronellal. 



Citral ozonide C 10 H 16 O 5 ; a water- white syrup; d 2 io 1,1486. 



Oenanthyl peroxide C H 3 (CH 2 ) 5 CH = O = O; from heptylic 

 aldehyde and ozone. When shaken with ice water it reproduces 

 heptylic aldehyde. 



Balbiano has submitted 1 ) in the form of a "memoria" to the 

 Reale Accademia dei Lincei, of Rome, his studies on the action of 



1 ) According to reprint kindly sent to us. 



