208 A GENERAL REVIEW OF 



This compound is converted, by treatment with silver oxide 

 and methyl iodide, into tetramethyl glucoseoxime methyl 

 ether. The oximido-group is evidently methylated, along 

 with the other hydroxyl groups, by the silver oxide reaction, 

 and that this is generally the case is shown by the application 

 of the reaction to other oximes. Thus oenanthaldoxime yields 

 a monomethyl ether, while salicylaldoxime and benzoin oxime 

 give dimethyl ethers under these conditions (Irvine and 

 Moodie, loc. cit.). 



Attempts have been made, by means of the silver oxide 

 reaction, to obtain evidence bearing on the constitution of 

 tetramethyl glucosephenylhydrazone, glucose phenylhydra- 

 zone, -p-toluidide, -p-phenetide, -/3-napthylamide, and 

 -o-carboxyanilide (Irvine and pupils (41, 42, and 56) ). The 

 compounds mentioned proved, however, to be so unstable 

 that molecular rupture resulted, and the method had neces- 

 sarily to be abandoned. The o-carboxyanilides of galactose, 

 rhamnose, mannose, and maltose were found to be similarly 

 unstable and to undergo decomposition when treated with 

 silver oxide and methyl iodide (Irvine and Hynd (63) ). 



PREPARATION OF BENZOIN DERIVATIVES 



By interaction of benzoin, silver oxide, and ethyl iodide, 

 Lander (4) obtained benzoin ethyl ether, 



C 6 H 5 .CH(OC 2 H 5 ).CO.C 6 H 5 . 



The reaction was carried out at the boiling-point of the 

 halide, and was seen to be accompanied by the formation of 

 water and of very dark silver residues. This last fact was 

 indicative of oxidation, and in addition to the benzoin ether, 

 benzaldehyde and ethyl benzoate were formed during the 

 reaction, probably as follows : 



fC 6 H 5 .CH(OH).CO.C 6 H 6 +Ag 2 = C 6 H 5 . CHO+C 6 H 5 C0 2 H+2Ag. 



2C 6 H 5 C0 2 H+Ag 2 = 2C 6 H 5 C0 2 Ag+H 2 0. 

 I C 6 H 5 C0 2 Ag+C 2 H 5 I = 2C 6 H 5 C0 2 C 2 H 5 +AgI. 



