JACKSON AND TORREY. — AN ORGANIC OXIDE. 



145 



The formation of the isoamylamine salt of oxydichlorisoamylamido- 

 quinone by the action of isoamyhimine on the oxide would begin by 

 the addition of one molecule of isoamylamine, forming the inter- 



Cll .OCH, 



CH3O OCOCeHj 



OxiJe. 



CgHuNH OCOCeHs 



O 



HO 

 CI 



CI 

 OCH, 



C.H„NH,HO- 



■^5^*^11 



CH3O OCOCgHs 



Intermediate Product. 



CI 



o 



Product. 



Ci 

 NHCsHu 



mediate product, which would then be followed by the conversion of 

 the acetal groups to the quinone, the replacement of the methoxy 

 group by the isoamylamido group C^HnNH, and the addition of a 

 molecule of isoamylamine to the hydroxyl. The two steps in this 

 conversion which might be regarded as doubtful are the conversion of 

 the acetal to the quinone by isoamylamine and the replacement of the 

 methoxy by the isoamylamido group. Fortunately, we have been able to 

 remove all doubt about both these steps by acting on the dichlordi- 

 methoxyquinonedimethyldibenzoylacetal, 



C,Cl2(CH30),(CH30)3(OCOCeH,)„ 

 with isoamylamine, wlien it was converted into dichlordiisoamylamido- 

 quinone, C6Cl2(C5HuNH)p.,. 



The formation of the sodium salt of the dimethylheraiacetal by the 

 action of sodic methylate on the oxide is explained in a similar way : — 



the formation of the intermediate addition product being followed by 

 conversion into a quinone, which then takes up two molecules of sodic 

 methylate to form the hemiacetal. 



The only other derivative of the oxide known is the reduction product * 

 obtained by Grindley and one of us by the action of hydriodic acid. This 

 substance gave upon analysis the formula CoC1.20CoH30H(OCOC|.H5)2, 



* These Proceedings, XXX. 442. 



VOL XXXIII. — 10 



