528 



SCIENCE 



[N. S. Vol. LIV. No. 1404. 



concentration of alkali used up to a certain con- 

 stant value. (g) The general effect of an in- 

 crease in temperature is that of an increase in 

 the yield of oxalic acid and carbon dioxide and 

 a decrease in the yield of acetic acid. 



The oxidation of propylene glycol with potas- 

 svum permanganate in the presence of potassium 

 hydroxide: W. L. Evans, (o) Acetic, oxalic and 

 carbonic acids are the final oxidation products of 

 propylene glycol with solutions of alkaline potas- 

 sium permanganate. (b) Acetic and carbonic 

 acids are the only products' obtained in neutral 

 solutions of potassium permanganate, (c) The 

 oialio acid production ia proportional to the 

 initial concentration of the alkali used. (<?) The 

 acetic acid production varies inversely with the 

 initial concentration of the alkali. (e) At 

 very low concentrations of alkali the produc- 

 tion of carbonio acid is proportional to the 

 initial concentration of the alkali. (/) The 

 production of acetic acid diminishes with an in- 

 crease in the temperature used, {g) The pro- 

 duction of carbonic acid increases with an in- 

 crease in the temperature used. (7») An increase 

 in temperature has no marked effect on the pro- 

 duction of oxalic acid. 



The condensation of citral, with certain Tee- 

 tones and the synthesis of some new ionones: 

 Harold Hibbeet and Laxjba G. Cannon. The 

 best method for purifying citral is the one de- 

 veloped by Tiemann. Of the condensing agents 

 hitherto employed, sodium ethylate is the most 

 satisfactory, but metallic sodium is equally effi- 

 cient. Better yields of a purer product have been 

 obtained. The bisulfite method of purification is 

 capable of general application in the purification 

 of pseudo-ionones, giving yields of about 85 per 

 cent, and chemically pure products. New ionones 

 have been synthesized from methyl propyl ketone 

 and acetophenone. 



The migration of acyl from nitrogen to oxy- 

 gen: L. Charles Eaipord and John E. CouTrrKE. 

 The present work is an extension and confirma- 

 tion of that previously published from this labora- 

 tory (J. Am.. Chem. Soc, 41, 2068 (1919)) and 

 was done to secure further evidence that the re- 

 arrangement involving migration of a lighter acyl 

 from nitrogen to oxygen, when a heavier acyl is 

 introduced into the molecule, is general for the 

 specific ease of acetyl and benzoyl, when the base 

 employed is an orthoaminophenol. The rear- 

 rangement was found to occur with the deriva- 

 tives of the base 2-amiuo-4-bromo-6-methylphenol. 



When the radicals were propionyl and benzoyl, the 

 rearrangement was not complete, which indicates 

 that the weight of acyl is one of the important 

 factors in this migration. 



Acylation with a-naphthoyl chloride and the 

 migration of acyl : L. Charles Raifoed and Clar- 

 ence E. Greider. (1) A further study of the 

 general reaction indicated in the above report 

 was carried out, using 2-aminophenol, 2-amiuo-4- 

 methyl-6-bromphenol, and 2-amino-4, 6-dibrom- 

 phenol as bases, and converting them into the 

 o-naphthoyl-acetyl and a-naphthoyl-benzoyl deriva- 

 tives, respectively. In each case the heavier acyl 

 was found on nitrogen, regardless of the order in 

 which they were introduced. (2) This study has 

 also furnished evidence, so far as it has been car- 

 ried, that a-naphthoyl chloride does not undergo 

 the Schotten-Baumann reaction. 



The migration of acyl: Effect of the relative 

 positions of the amino and hydroxyl groups: L. 

 Charles Eaiford and H. A. Iddles. In a con- 

 tinuation of the studies mentioned above, the 

 acetyl-benzoyl derivative of 2, 4-dibrom-3-methyl- 

 6-aminophenol was found to undergo the rear- 

 rangement, and benzoyl was found on nitrogen; 

 while the derivative of the isomeric base, 2, 6- 

 dibromo-3-methyl-4-aminophenol did not suffer 

 the migration. Here it was possible to isolate 

 N-acetyl-0-benzoyl, and 0-acetyl-N-benzoyl de- 

 rivatives. The failure of this para compound to 

 undergo this change was supported by the be- 

 havior of the derivatives of 4-aminophenol, 2, 6- 

 dibrom-4-aminophenol, and 2-brom-4-amino-6-meth- 

 ylphenol. 



Stability of the C-Hg linkage in m,ercury 

 derivative of maleric acid. Preliminary paper: 

 Frank C. Whitman and B. J. Martin. The 

 sodium salt of hydroxymercuric maleric acid ob- 

 tained from the action of sodium hydroxide on the 

 reaction product of maleric acid with mercuric 

 acetate contains an unstable C-Hg linkage. It 

 reacts at once with sulfides. With sodium iodide 

 it gives sodium maleate, sodium mercuric iodide 

 and sodium hydroxide. The reaction is complete 

 only on heating the mercury compound with a large 

 excess of iodid. The calculated amount of iodide 

 gives only one third of the calculated amount of 

 base. If this base is neutralized and the mixture is 

 boiled a little more base is formed. Many repeti- 

 tions of this process give a total amount of base 

 which gradually approaches the calculated volume. 

 Charles L. Parsons 



Secretary 



