( 278 ) 



Some time ago ') I poiiiicMl oiil (he possihilily of llic existence of 

 a similar iiilermedialc in-odiict in llic li-.iiisroi-iiiadoii of liNdi-ohciizoiii 

 into diplieiijlacelaldeliydc 



Am A[ 



H— C C-CJl, ^ H-C -.C-CJi. 



but at the same time 1 liaxe shown experimentally 1 lie iiieoiTcetness of 

 (hat snpposilion. In an appended note I have already observed that 

 in view of my resnlts obtained, the theory of Nef was not aeoeplable. 

 It api)eared to nie therefore, to be of imi)orlan('e to extend my 

 researches also to a derivative of benzpiiiacojie and (hns to form a 

 defmite opinion as to the correctjiess or incorrectness of Nf-f's theo- 

 retical explanation. 



For this research I took 44'4"4"' tetrachlorobenzpinacone obtained 

 by reduction of 44' dichlorobenzophenone. On being heated with acetyl 

 chloride it passes into tetrachlorobenz|)inacoline. If this is boiled 

 with alcoholic potassium hydroxide it is resolved into ti-ichlorotri- 

 phenylmethane and p. chlorobenzoic acid according to this scheme: 

 ((4) . 01 0,H J, : OOH . OOH : (0„H, 01 (4)), -^ 



((4) . 01 . C„H,).,^ 

 -^ >0— 00— 0„H,01(4) -> 



? 01 o,h/ 



((4) . 01 . C.EXx /" 



-^ >0H + OJI, .01(4). 



? CI . o.h/ \^ ^^j 



This trichlorotri[)henylmethaiie now a|)|)eared to be identical with the 

 44'4' trichlorotriphenylmethane obtained from 44'4" triaminotriphenyl- 

 methane (p. leucanilinc). This explains the para-posilioii of all chlorine 

 atoms ill the tirst-named trichlorotriphenylmethane. This further shows 

 that the phenyl groiq) is attached to the same 0-atom before aiul 

 after the migration and that therefore the intermediate product as 

 suggested by Nff is an impossibility. The exi>lanatioii gixcn bv Nkf 

 for this intramolecular atomic reai-rangement is, therefore, incorrect. 



The \iews held as to the transformation of «-glycols into aldelndes 

 are tu'o in number: 



1) Rec. 21. p. 30. 



