JACKSON AND GKINDLEY. — ACETALS FROM QUINONES. 40& 



xvm. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ACTION OF SODIC ALCOHOLATES ON CHLORANIL. 



ACETALS DERIVED FROM SUBSTITUTED 



QUINONES* 



By C. Loring Jackson and H. S. Grindley. 



Presented May 9, 1894. 



Introduction. 



During the study of the action of sodic alcoholates, sodium malo- 

 nic ester, and similai* reagents upon tribromdinitrobenzol and related 

 substances,! carried on now for some years in this Laboratory, it has 

 been observed repeatedly that one of the atoms of bromine is replaced 

 by hydrogen. In all this work, however, the bromine replaced by 

 hydrogen has stood in the meta position to two other atoms of bro- 

 mine, and, as it was possible that this strange reaction depended on the 

 symmetrical position of the three atoms of bromine, we undertook the 

 study of a substance with a different constitution ; and for this pur- 

 pose selected chloranil, in which no one of the atoms of halogen is in 

 the meta position to two others. While this substance was well fitted 

 for our work, because the atoms of chlorine which it contains can be 

 replaced with comparative ease, on the other hand the action of most 

 of these reagents with it had been already studied by Stieglitz,+ Ikuta,§ 

 Kehrmann.ll and others, and in no case could we find any mention of 

 a direct replacement of chlorine by hydrogen ; but still as it was 



* The work described in this paper formed a thesis presented to the Fac- 

 ulty of Arts and Sciences of Harvard University for the Degree of Doctor of 

 Science, by H. S. Grindley. 



t These Proceedings, XXIV. 1, 234, 256, 271, 288 ; XXV. 164 ; XXVII. 280 ; 

 XXIX. 228. 



J Am. Chem. Journ. XIII. 38. 



§ These Proceedings, XXVI. 295. 



II Journ. Prakt. Chem., [2.], XL. 365. 



