Ga Pv os 
ys 3 
lohexenones of the ivone xe type. He Sicocdded t in two cases, viz.:— A-1.1. 2-trimethyl- 
eyelohexene-6one and A®-1.1.2. 5-tetramethylc, yclohexene- -6-one —, the yields, however, 
were extraordinary low. and hardly permitted of the peeRaTiion of the corresponding . 
: nicarbazones. For this reason, we abstain from entering into details on this paper — 
Raich as we own, offers many interesting results in theoretical respect. ae 
_ Isodicamphor. ae Some time ago, A. Haller?) demonstrated that sodiocamphor reacts 
T eadily with ketones oe aldehydes with formation Sa bodies of the general type of di- 
Lae C(CoHs)2. : 
phenyleamphomethane: — ee . In a like manner, M. Guerbet*) expected 
to obtain bornylene camphor‘) by es of an with ae ene: This body 
: actually formed on heating camphor with a solution of sodium in methyl alcohol, 
termed isodicamphor and which is isomeric with Oddo’ 's°) dicamphor (m. p. 155 to 
bromocamphor. . niiaa ad 
es oo | A aie oe 
5 ctu l oe cet = uk Hef Gt ee 
aia ~ Camphor. aes A ee aA abt ee . 
For the preparation of isodicamphor, Guerbet heated eaiphiee with a solution of 
ae in methyl alcohol under pressure (in a closed beer bottle) for three times 
24 hours ina water-bath; the methyl alcohol and. the excess of camphor is then driven ie 
‘off by steam-distillation and the residue, _impure isodicamphor, purified by recrystallisa- | 
tion from alcohol. 100 g. camphor yielded 25 g. dicamphor. The mother-liquors con- _ 
tained a second body, the nature of which Guerher -was not. yet able to investigate. 
femperature to 180°. After crystallisation from alcohol, isodicamphor forms small 
“thombohedra, m. p. 196°, with a weak smell recalling camphor; [~]p +-64° 54’ (one-half 
Sramme-molecule dissolved in one liter of absolute alcohol). On heating to 200° the 
body sublimed nearly without decomposition; at 250°, it is retransformed into ‘camphor. 
The monoxime melted at 160°, the dioxime at 235°. - When dissolved ‘in carbon 
disulphide, isodicamphor reacts with bromine with formation of monobromo_ iso- 
dicamphor (m. p. 161°) and dibromo isodicamphor (m. p. 132°), the latter originating 
also on treatment, in a sealed tube, of isodicamphor with the calculated amount 
“of bromine to 100°. When ‘oxidised with diluted nie acid, isodicamphor mlelds 
Camphoric acid. 
_ Guerbet points out finally ¢ that the same process in the formation of isodicamphor ; 
— the splitting of one hydrogen atom each from two molecules of camphor in presence 
of an alcoholate — has been observed by Haller®) when heating camphor with the 
sodium compounds of propylalcohol, isobutyl, and benzyl alcohols. Here, in addition 
© the alkyl camphors and alkyl borneois, the corresponding alkylidene eephers were 
romed from the alisyl camphors by loss of water. 
.. 
f 
4) Helv, chim. ere 2 (1919), 144, a, 2) Soi rend. 142 (1906), 971. — *) Ibidem 166 (1918), 1049. — 
Tbidem 149 (1909), 934; Report April 1910, 179. — 5) Gazz. chim. ital. 27 (1897), I. 159. — 8) Compare, 
r instance, tigi rend. 142 (1906), 1309; Report ho Balle 1906, 134. 
f Li* 
but in very minute quantity; the chief product was a body CsoHjoO which the author Nae 
156°) formed, inter. alia, on action of water on the reaction- ee from Se ‘and. 
The bornylene camphor mentioned above results in this reaction only on raising the : 
