CUPRIC CHLORIDE ON ORGANO-METALLIC DERIVATIVES OF MAGNESIUM. 37 



THE ACTION OF OUPRIO CHLORIDE ON ORGANO 

 METALLIC DERIVATIVES OP MAGNESIUM. 

 By Eustace Ebenezbr Turner, b.a., m.Sc, a.t.c. 



[Read before the Royal Society of N. S. Wales, June 2, 1920.'] 



It has been shown 1 that an ethereal solution of phenyl 

 magnesium bromide reacts with anhydrous cupric chloride 

 to give an almost theoretical yield of diphenyl : 

 2 0n01 2 + 2 PhMgBr = Ph.Ph + Cu 2 01 3 +MgCl 3 -|-MgBr 2 . 



This method of preparing diphenyl is preferable to that 

 described previously 2 using chromic chloride, since the 

 anhydrous cupric chloride may readily be made by dehydrat- 

 ing the commercial dihydrate. Moreover, in the case of 

 o-tolylmagnesium bromide and iodide, chromic chloride 

 gave a very poor yield of 1 : l^ditolyl, whereas it has now 

 been found that anhydrous cupric chloride reacts with 

 o-tolylmagnesium bromide to give the ditolyl in good yield. 

 That the preparation of this hydrocarbon has presented 

 some difficulty in other hands may be judged from the fact 

 that Kenner and Turner 3 rejected the Fittig method in 

 favour of that due to Ullmann. 4 



Attempts to couple two dissimilar groups by means of the 

 cupric chloride reaction have met with no success, as was 

 the case with chromic chloride. Since there is no obvious 

 reason to expect a better yield of (say) toluene in the 

 Fittig reaction: 



Ph. 1 + 2 Na + Me. I = 2 Na I + Ph.Me, 



1 Trans. Chem. Sou., 1919, 115, 559. 



2 Trans. Chem. Soc, 1914, 105, 1057; this Journal. 1919, ltii, 100. 



3 Trans. Chem. Soc, 1911,99, 2103. 



4 Annalen d. Chemie, 1904, 332. 28. 



