CUPRIC CHLORIDE ON ORGANO-METALLIC DERIVATIVES OF MAGNESIUM. 39 



7*3 grams of magnesium and 200 cos. of ether. A vigor- 

 ous reaction set in and was finally carried to completion 

 by heating on the water bath. The orange-red solid 

 (possibly an organometallic derivative of copper) was 

 decomposed with water and dilute acid, the organic portion 

 extracted with ether, and the extract dried, filtered and 

 evaporated. The residue was distilled under diminished 

 pressure and gave a yield of 1 : F-ditolyl corresponding to 

 30 per cent, of the theoretical. The hydrocarbon was very 

 pure and melted at 18°. 



Attempt to prepare a-Benzylnap\ithalene. 

 Benzyl bromide and magnesium react in presence of 

 ether to give not only benzyl magnesium bromide but also 

 considerable quantities of s-diphenylethane, the formation 

 of the latter being decreased if a large excess of magnesium 

 is present. The mixed Grignard reagents were therefore 

 prepared by allowing 34*2 grams of benzyl bromide to react 

 with 9*73 grams of magnesium in presence of 200 ccs. of 

 ether, 41*4 grams of a-bromonaphthalene being added when 

 the whole of the benzyl bromide had reacted. To the 

 solution finally obtained were added 60 grams of cupric 

 chloride. A brisk reaction set in, was carried to comple- 

 tion by heating, and the product worked up as described 

 above. Distillation under diminished pressure gave traces 

 of toluene and naphthalene, but chiefly s-diphenylethane 

 and a : a'-dinaphthyl. No «-benzylnapthalene could be 

 detected. 



Formation of s-Diethylsuccinic diethyl ester. 

 a-Bromobutyric ester (19*5 grams) was added to 2*43 

 grams of magnesium and 200 ccs. of ether. As soon as a 

 vigorous reaction had set in, 20 grams of cupric chloride 

 were added. Steady reaction proceeded for about half an 

 hour and allowed to become complete at water bath tem- 

 peratures. The resulting mixture, on decomposing in the 

 usual manner, gave 3*5 grams of s-diethylsuccinic diethyl 

 ester. 



