NOTES ON SCIENTIFIC RESEARCH. 83 
of which is outside the nucleus, as well as from some aliphatic «/-unsaturated ketones. 
They obtained anhydropulegonehydroxylamine by treating pulegonehydroxylamine with 
an ethereal solution of hydrogen chloride gas. If the hydrochloric acid is allowed to 
act longer, the normal pulegoneoxime seems to form. Camphorone, when boiled with 
hydroxylamine hydrochloride and sodium bicarbonate in alcoholic etheral solution, 
passes into camphoronehydroxylamine, melting at 120°. With hydrochloric acid in 
ethereal solution it forms, anhydrocamphoronehydroxylamine, an oil that smells like 
coniine. It seems to convert itself into camphoroneoxime (m.p. 115°) when kept in 
contact with water. The oxalate melts at 170°. 
Methylheptenone. In his 118 treatise on terpenes and essential oils, O. Wallach‘) 
reports on the derivatives of methylheptenone and allied compounds. Three isomerides 
of methylheptenone are possible, owing to the different position of the double linking. 
They may be distinguished as «8- and y-methylheptenone (the better known). There 
is, besides, a 0-isomeride, unknown so far. 
All the four modifications, on addition of hydrogen to the ethylene linking, ought to 
yield the same saturated methylheptanone (a methylhexylketone), which Wallach prepared 
some time ago by reducing °-methylheptenone with palladium and hydrogen’). It was 
made evident by experiments that the ethylene linking in «?-position absorbs hydrogen 
more readily than that in »0-position. «-Methylheptenone in alcoholic solution can be 
reduced with sodium to the saturated methylheptanol, whereas y-methylheptenone 
yields under the same conditions methylheptenol as final product. ; 
The so-called isomethylheptenone, an isopropylbutenyl ketone, is isomeric with the 
methylheptenone just mentioned. The derivatives of isomethylheptenone smell quite 
different from the analogous ones of y-methylheptenone. Whilst the odour of these is 
pleasant, that of the others is sharp and rather disagreeable. The position of the 
oxygen in the molecule is thus very noticeable. 
By treatment with magnesium ethyl iodide, methylheptanone yields tetrahydro- 
linalool, an alcohol which Barbier also prepared a short while ago®). By splitting 
off water with the aid of zinc chloride, tetrahydrolinalool afforded a hydrocarbon, 
(CHs)2 CHCH2 CH, CH, C(CHs) : CHCHs, which on oxidation with potassium permanganate 
passed into methylheptanone (semicarbazone, m. p. 156°). The same hydrocarbon is 
obtained by treatment of methylheptanone with zinc and ethyl bromopropionate. The 
experiments with a view to prepare from the nitrosate of the hydrocarbon an un- 
saturated ketone with 10 carbon atoms had not the desired success. 
The action of hypobromite on methylheptanone leads to heptoic acid. Through 
the action of several molecules of bromine on methylheptanone, and consecutive 
treatment with alcoholic alkali, an acid is formed that contains 8 carbon molecules. 
Sufficient explanation for this behaviour was found in the course of the investigation. 
The isopropyl-n-butylketone, obtained on reducing isopropylbutenyl ketone (iso- 
methylheptenone) according to Paal or Skita, boiled between 158 and 159°. The 
reduction of the ketone in moist ethereal solution leads to isopropyl-n-butylcarbinol 
(b. p. 167 to 168°), in addition to a pinakone. The interaction of csopropylbutenyl 
ketone and isopropylbutyl ketone with Grignard’s reagent does not take place so smoothly 
1) Liebigs Annalen 408 (1915), 183. — *) Comp. Report April 1911, 165. — *%) Comp. Report April 1915, 90. 
6* 
