OF ARTS AND SCIENCES. 211 



maux* from uitrobenzaldehyd, until Wachendorff,t in 1875, described 

 the orthonitrobenzylbromide aud chloride. Soon after, iu a preliminary 

 notice! of a portion of the work contained in these papers, the para- mela- 

 and orthobrombenzylbromides were described ; finallj^, in 1877,Wachen- 

 dorff published a very interesting paper § upon the nitrobenzylchlorides 

 aud bromides, in which he described the metanitrobenzylbromide, and 

 called attention to the striking foct that metanitrobenzylchloride could 

 not be obtained under conditions which gave without difficulty the 

 paranitrobenzylchloride, while he had not as yet succeeded in obtain- 

 ing the orthonitrobenzylbromide under the conditions which furnished 

 both of its isomeres ; he said, however, that he did not despair of ob- 

 taining it by new'experiments under different conditions ; from this it 

 would seem probable that the statements made in his preliminary 

 notice in regard to orthonitrobenzylchloride and bromide, have been 

 proved incorrect by his later exi^eriments. 



The object of these papers is to add to our knowledge of this little 

 studied class of compounds, and, also, to make some comparisons be- 

 tween the replaceability of the haloid atoms in the side-chain, which it is 

 hoped may in the future throw some light upon the nature of chemi- 

 cal attraction. The substituted benzylbromides have been used as the 

 starting-point for each class of compounds, because these substances 

 can be easily obtained by the action of weighed amounts of bromine 

 upou the corresponding substituted toluols in the state of vapor. This 

 action of bromine on boiling toluol was first studied by Lautli and Gri- 

 mauxjll Cannizaro,ir and Beilstein,** who proved that the substance thus 

 formed was identical with the benzj^lbromide previously obtained by 

 Kekule ft from benzylalcohol by means of hj^drobromic acid. 



FIRST PAPER. 

 OX CERTAIN SUBSTITUTED BENZYLBROMIDES. 



C. LoKiNG Jackson. 

 p 

 Parabromhenzylbromide {C^H^Br.CH.^Br.). — Preparation. First 



Method. Ten grammes of pure parabromtoluol, melting-point 28.5°, 



* Grimaux, Comptes Rend., LXV., p. 211 ; Ann. Chem. Pharm., 145, p. 46. 

 t Wachendorff, Ber. D. Ch. G., 1875, p. 1101. 



I Jackson, ib., 1876, p. 931. 



§ Wachendorff, Ann. Chem. Pharm., 185, p. 259. 



II Lauth and Grimaux, Bull. Soc. Chim. [2], VII., p. 108. 

 II Cannizaro, Ann. Chem. Pharm., 141, p. 198. 



** Beilstein, ib., 143, p. 369. 

 tt Kekule, Ann. Chem. Pharm., 137, p. 188. 



