418 PROCEEDINGS OF THE AMERICAN ACADEMY. 



itself. If this iuterpretation of the observation is true, it has no bear- 

 ing ou our theory, as it shows only that the phenoquinoue is easily 

 decomposed by alkalies, this decomposition taking place before it had 

 time to form a salt. We then tried the action of sodic phenylate on 

 quinone, as according to our theory this should act as well, or even 

 better than free phenol, and we have succeeded in getting an action in 

 this case, a strongly colored product being formed ; but these experi- 

 ments were undertaken so late in the year that we had no time to 

 isolate this substance for study. We should add that in the action 

 of potassic phenylate on chloranil, described at the beginning of the 

 experimental part of this paper, there are strong indications of the 

 formation of a diphenylhemiacetal, as the liquid took on a blue-black 

 color in the cold, which upon heating changed to the red of the di- 

 chlordipheiioxyquiuone. The isolation of this hemiacetal, if possible, 

 will throw a great deal of light upon our theory of the nature of 

 phenoquinoue. All these lines of work will be taken up in this Labo- 

 ratory during the next academic year, and we hope that by means of 

 these experiments we shall succeed in testing thoroughly our theory 

 that quinhydrone and phenoquinone are hemiacetals of quinone. The 

 curious addition compounds of the nitranilines and quinones * will also 

 be considered in this connection. 



The dichlordimethoxyquinone dimethylhemiacetal 



C6Clo(OCH3)o(OII),(OCH3)„ , 



although most conveniently made from the dichlordiphenoxyquinone 

 by the action of sorlic methylate, can also be obtained by the action of 

 the same reagent on diclilordimethoxyquinone, or even on chloranil. 

 In this last case the first product is a green sodium salt, which by treat- 

 ment with water yields the sodium salt of the hemiacetal and the 

 tetrachlorhydroquinone, mentioned at the beginning of this paper. 

 With sodic ethylate and chloranil we have not succeeded in obtaining 

 the cnrrespotiding ethyl compound ; it may be, however, that this 

 result was due to not finding the proper conditions for .the reaction. 

 The dichlordiethoxyquinone tetraethylacetal 



C6Clo(OaH,,),(OCoH5), , 



alluded to in the discussion of the constitution of the hemiacetals, was 

 made by the action of ethyliodide in the cold on the silver salt of the 

 corresponding hemiacetal. The yield was exceedingly small, most of 



* Hebebrand, Ber. d. eh. G., XV. 1973; Niemayer, Ann. Chem., CCXXVIII. 

 332. 



