JACKSON AND TORREY. AN ORGANIC OXIDE. 143 



la Formulas I. and II. the attachment is to two atoms of carbon in the 

 para position, which in I. are the quinone atoms of carbon, in II. those 

 which are attached to the hydroxyls in chloraniHc acid. Formula HI. 

 represents the oxygen attached to two atoms of carbon in the ortho 

 position; and Formula IV. shows a meta attachment. Of the formulas 

 we considered I. or II. the most probable, and devoted ourselves at first 

 to the study of these. 



The conversion of the substance into chloranilic acid by the action of 

 hot sodic hydrate can be easily explained by all four of these formulas, 

 and therefore gives no aid in distinguishing between them. 



Isoamylamine converts the oxide into the isoamylamine salt of oxydi- 

 chlorisoamylamidoquinone, which has the following formula : — 



In forming this substance from a body having Formula I. it is neces- 

 sary that the two methoxy groups should be acted on differently by 

 the isoamylamine, since one of them is replaced by the isoamylamido 

 group (CgHiiNH), and the other converted into the phenol salt group 

 (CsHuNHoHO). Such an action would be highly improbable theoreti- 

 cally, as these two methoxy groups are symmetrically disposed in this 

 formula ; and it is proved to be impossible by our study of the action of 

 isoamylamine on the similarly constituted dichlordimethoxyquinonedi- 

 methyldibeuzoylacetal, C6Clo(OCH3),(OCH3)2(OCOC,H5).,, which was 

 converted by it into dichlordiisoamylamidoquinone, C6C1.2(NHC5Hi])202. 

 Formula I., therefore, is not in harmony with these observations, and 

 must be rejected. Formulas II., III., and IV. can be easily brought into 

 harmony with the results of the experiments with isoamylamine, as will 

 be shown later. 



Sodic methylate converted the oxide into the sodium salt of the 

 dichlordimethoxyquinone^imethylhemiacetal, which has the following 

 formula : — 



NaO OCH3 



CH30 



CI 



CI 

 OCH3 



CH3O ONa 



