NOTES ON SCIENTIFIC RESEARCH. #3 
this supposition as proved, for it is not impossible that the citronellal semicarbazone 
is a very difficultly separable mixture of two semicarbazones. 
A new type of decomposition of ozonides by water was discovered by the isolation 
of acetylcarbinol, CH;-CO-CH2OH, from the products of decomposition of citronellal and 
citronellol ozonides. This reaction may be explained by supposing that citronellal adds 
ozone in a normal way and that the following peroxide-like transposition takes place: 
a | nena >cO + OCH... 
Nea Oe fase H2Cé 
The quantities of acetylcarbinol found were very small. No acetylcarbinol formed in 
the transposition of the ozonide of citronellalsemicarbazone. 
In the experimental part of the paper we find particulars about the preparation 
and’ the properties of pinene ozonide. Harries conducted ozone, the ozone content 
of which had been reduced as far as 9.3 to 4.8 p.c. by washing with a 5 p.c. soda lye 
and concentrated sulphuric acid, into a solution of pinene from French turpentine oil 
in hexane, until no more bromine was added, thus obtaining a solid ozonide, Cio Hie Os, 
and a syrupy ozonide, which became very frothy in a vacuum. Besides, an oily body 
of unknown composition had formed. The best yield of solid ozonide was obtained 
with the aid of a freezing mixture. 
cycloHexene yields a monomeric liquid ozonide of pungent disagreeable odour and 
a solid polymeric ozonide which explodes violently at about 140 to 150° 
Harries obtained from cyclopentene, in addition to the already known normal, viscid 
ozonide, an explosive polymeric as well as a non-explosive polymeric ozonide. 
HC Ci 
oe Greer Ct. G1 (GH:)- Ch, CHO CO 
(I) Citronellal. C 
| Hc cH 
CHs:- en CH2-CH:2- CH: CH -CH,CHO H.C Gi. 
O CHs CH-CHs 
(II) Methyloctanonal peroxide. | (Ill) Ethanoyl-4-methylcyciohexene-1. 
(H3C)eC : CH: CHa: CH, - CH (CH): CH, CHO 
(IV) Rhodinal. 
32 Gas Sia & 
sC-HC\ CH 
ie NK 
(VI) Methyloctanonal monosemicarbazone. 
C-CO.H 
(V) 5-Methylcyclopentene HO se £ CH, ° CH, ; CH (CHs) a CH, : CH o N : NH $ CO : NH, 
carboxylic acid. (VII) Semicarbazone of the half-aldehyde of )-methyladipic acid. 
He further made an interesting observation as to the by-products formed in the 
preparation of cyclopentene. The reduction of cyclopentanone to cyclopentanol, which 
serves for the preparation of the cyclopentene, takes a different course, according to 
whether it is carried out with sodium and absolute ether or with sodium and ordinary 
ether. As the latter always contains alcohol, which with the sodium forms sodium 
