122 
melting point 84° to 85°. Potassium bisulphite splits off water from 
the alcohol, with formation of a hydrocarbon CgH^g, pulenene 
(boiling point 60° to 65° [12 mm]), whose nitrosate melts at 98° to 
99^, whilst zinc chloride yields an isomeric hydrocarbon boiling at 145° 
to 150^, which does not form a soHd derivative with amyl nitrite and 
nitric acid. 
Whilst the oxidation of pulenone with potassium permanganate 
in addition to oxalic acid and acetic acid yielded only small quan- 
tities of acids which could throw a light on the constitution of the 
ketone, there could be isolated, by means of chromic acid anhydride in 
solution of sulphuric acid, first a bicarboxylic acid C9 H^g O4 of the melting 
point 114° to 115°, secondly, a ketonic acid CgH^^Og of the melting 
point 49° to 51° (melting point of the semicarbazone 150° to 151°), 
thirdly as-dimethyl succinic acid CqH^qO^ (melting point 140°). The 
bicarboxylic acid C9H-^g04 could be identified as a, yS, /J-trimethyl adipic 
acid by means of conversion into a, a, a'-trimethyl pentanone (boiling 
point 152° to 153°, melting point of the oxime 60° to 62°; melting 
point of the semicarbazone 150° to 151°), and oxidation thereof into 
the ketonic acid obtained above and further into a, a-dimethyl 
glutaric acid (melting point 82°). The following summary may illustrate 
the reaction. 
CH — CH. 
CH, 
H,C 
\ / 
CO 
HjC 
i 
H3C- 
- CO 
ketonic acid 
HjC 
H,C 
\ / 
COOH 
HjC 
CH — CH3 
COOH 
COOH 
C(CH3)., 
CH — CH3 
CO 
C(CH,), 
COOH 
trimethyl adipic acid 
trimethyl pentanone 
HOOC — CH2C(CH3)2COOH ^ CH^ — CH^C (CHg)^ • COOH. 
Pulenone oxime (boiling point 117° [12 mm]; melting point 94° 
to 95°), when treated with phosphorus oxy chloride is converted into 
an isoxime of the melting point 96° to 97° and the boiling point 
145° to 150° (27 mm), which w^ith acids yields, with loss of water, 
nonylenic acid nitrile (boiling point 89° to 90° [10 mm]; 216° to 
217° [760]). The latter is also formed direct from the oxime on 
treatment with phosphorus oxychloride and phosphorus pentachloride. 
