288 



SCIENCE PROGRESS 



by preparing the monobromo additive compounds of morphenol- 

 methylether and acetylmorphenol which, by the further action 

 of bromine, are converted into the dibromo derivatives corre- 

 sponding to dibromophenanthrene — i.e. the bromine atoms 

 must be attached to the "bridge" carbon atoms: 



HO 



Dibromophenanthrene 



Dibromomorphenol 



The validity of this conclusion has been confirmed in the 

 following manner by the same investigator. 1 By first converting 

 morphenol into an acetyl compound, and then oxidising by 

 chromic acid in glacial acetic acid, he has succeeded in pre- 

 paring a quinone which yields a phenelzine on treatment with 

 orthodiamines. The body so obtained has properties similar 

 to the phenazine of morpholquinone, and is therefore to be 

 regarded as a derivative of phenanthrazine. Hence it follows 

 that both the "bridge" carbon atoms of morphenol have 

 been oxidised to form an ortho-diketone, while the oxygen 

 ring has remained unopened, and therefore the only possible 

 formulae for morphenol and morphol are : 



HO 



HO 



HO 



Morphenol 



Morphol 



This was confirmed by Pschorr and Sumuleanu, 2 who suc- 

 ceeded in synthesising dimethylmorphol. They obtained 

 a-phenyl-2-nitro-3, 4-dimethoxycinnamic acid by the condensa- 

 tion of Wc.o-nitrovanillin-methylether with sodium phenylacetate 

 by means of Perkin's reaction. This was converted into the 



1 Ber. 33, 352. 



2 Ibid. 33, 181 1. 



