21 
a compound is formed of 1 mol. of oxide and 1 mol. allylamine. 
By distillation and recrystallisation from petroleum ether, | obtained 
white needles melting at 37,5°. The oxide when heated with am- 
monia also gave a crystallised amino-aleohol. 
Another method often applied to arrive at internal ethers consists 
in addition of hypochlorous acid to an unsaturated hydrocarbon and 
subsequent elimination of hydrogen chloride from the chlorhydrine 
formed. Before applying this method to hexatriene which might yield 
an oxide of the formula C,H,O, I first tried the action of this acid 
on a hydrocarbon with only one conjugated system of double bonds. 
CH, 
The hydrocarbon CH,=C—CH=—CH,, isoprene, which is now 
te Peo dees Ay 
readily prepared in a pure condition by means of the so-called 
Harrizs isoprene lamp, was cooled in ice-water and shaken in the 
dark with a solution of hypochlorous acid in such proportion that 
1 mol. of acid was used for 1 mol. of isoprene. 
‘The hypochlorous acid disappears spontaneously and the isoprene 
dissolves. After saturation of the liquid with common salt, ether 
extracts from this solution a compound boiling at 142°—145°, the 
chlorine content of which points to its having the composition 
C,H,OCI. By removing from this compound hydrogen chloride by 
means of strong aqueous potassium hydroxide, I obtained a liqnid 
with an ethereal odour b.p. 80’—82° which, however, still contained 
a trace of halogen. 
Brought into contact with hydrogen chloride the latter is at once 
absorbed ; when dissolved in carbon tetrachloride, the substance 
decolorises, although slowly, a solution of bromine. 
If now we consider to which position in the isoprene molecule 
the HOCI can be attached the three following possibilities may occur. 
1. The hypochlorous acid is attached to the double bond 1==2. 
2. The hypochlorous acid is attached to the double bond 3=4. 
3. or, because the two double bonds are in conjunction, the linking 
has taken place at the carbon atoms 1 and 4 with the appearance of 
a new double bond between the carbon atoms 2 and 3. In the latter 
case a 5-ring would, probably, have been produced from the chlor- 
hydrine thus formed, namely a methyldihydrofurane. The ready 
absorption of hydrogen chloride does not, however, support the latter 
view. 
I hope to be soon able to make further communication on this 
subject with which I am still occupied. 
Utrecht, April 1912. Org. Chem. Lab. University. 
