526 



SCIENCE 



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



or phosphorus the principal product is 2,4-di- 

 chloroformanilide. With thionyl chloride, however, 

 the following products were isolated : 2,4-dichloro- 

 formanilide, phenylimido phosgene, and mono- 

 and di-ehloro phenylimido phosgene. The last 

 three compounds were identified by their conver- 

 sion into the corresponding triphenyl guanidines, 

 urethanes, and aeetanilides. 



The preparation of diaVkyl mercury compounds 

 from the Grignard' reagent: C. S. M.uivel and 

 V. L. GoTJLD. Diphenyl mercury, dibenzyl mercury 

 and dieyclohexyl mercury have already been pre- 

 pared from the Grignard reagent and mercuric 

 chloride, but only in poor yields. This method 

 may be applied to the preparation of various di- 

 olkyl mercury compounds in yields of 45-65 per 

 cent., if the proper precautions are taken. In this 

 reaction there is formed first, an alkyl mercury 

 halide which is then converted into the dialkyl 

 compound. The first step goes easily but a large 

 excess of the Grignard reagent and long heating 

 are necessary to bring about the second. The 

 unreacted magnesium must be removed from the 

 Grignard reagent solution in order to avoid re- 

 duction of the mercuric halide and consequent 

 lowering of the yield. 



T}ie ohlorination of 5-hydroxy-l,4-naphthoqui- 

 none (juglone) : Alvin S. Wheelee and Paul 

 E. Dawson. The chlorination of juglone in hot 

 glacial acetic acid solution yields dichlorojuglone 

 (A), probably the 2,8-isomer, orange red needles, 

 m.l51°. Benzoyl derivative, yellow needles, m. 225°. 

 Sodium salt, indigo blue, a direct dye for silk and 

 wool. AleohoUc caustic soda gives a monochloro- 

 hydrosy-juglone, yellowish brown needles, m.l91°. 

 Diacetyl derivative, yellow needles, m.l47°. Mono- 

 chloro-anilino-juglone, obtained by boiling A with 

 aniline in alcohol, violet red needles, m.222° ; 

 o-toluino derivative, dark red needles, m.l51°; 

 p-toluino derivative, deep violet needles, m.235°. 

 So far no oxidation products of A have been ob- 

 tained which might locate the chlorine atoms. 



Kelp tar oils: Alvin S. Wheeler and H. M. 

 Taylor. The kelp tar oils came from the Summer- 

 land, California, kelp plant of the U. S. Depart- 

 ment of Agriculture and were given to us for 

 study by Mr. J. W. Turrentine, in charge. The 

 oil is a mixture of compounds, for we found the 

 boiling point to range from 200° to 300° at at- 

 mospheric pressure and from 50° to 170° at 12 

 mm. In the latter case two thirds of the distillate 

 came over between 110° and 150° and 25 per cent, 

 of the oil remained behind as pitch. The oils dis- 



solve in all organic solvents and are unaffected 

 by most reagents. The reaction with bromine is 

 violent and hydrobromio acid is evolved. The re- 

 distilled product contains bromine. Moleculax 

 weight determinations of fractions from low to 

 high boiling points gave values from 124 to 165. 

 Specific gravity ranges around the point 0.94 and 

 refractive index about 1.46. Hydrogenation and 

 brominatiou studies are in progress. 



Tlie structure of disalicylaldehyde : ROOER 

 Adams and M. F. Fooler. When salieylaldehyde 

 is heated with acid chlorides, it is converted into 

 disalicylaldehyde, a white solid, m.l31°. This 

 substance has been studied by previous investiga- 

 tors and shown to have the following properties: 

 empirical formula CiiHioO,, stable to sodium hy- 

 droxide solution, unstable to concentrated sul- 

 phuric acid yielding two moles of salieylaldehyde; 

 shows no reaction which would indicate a phenol or 

 'aldehyde group; No satisfactory formula has yet 

 been suggested for this substance. The following 

 one is proposed: 



This structure is a double acetal and agrees with 

 the properties above mentioned. The synthesis of 

 analogous compounds which have the same chemi- 

 cal properties has been accomplished. New meth- 

 ods of preparation for disalicylaldehyde indicate 

 that it has an acetal structure. 



Anthraquinone thioethers: JI. S. Hoffman and 

 E. E. Eeid. The study of the replacement of the 

 sulphuric acid group in alpha anthraquinone sul- 

 phonic acid has been continued with the use of a 

 variety of mereaptans, isopropyl, benzyl, nitro- 

 benzyl, monothio-glyeol, etc., and a great variety 

 of anthraquinone thioethers thus prepared. Most 

 of these have been oxidized to the sulphones. 



Some derivatives from p-nitrothiophenol: W. E. 

 Waldeon and E. E. Eeid. A large niunber of 

 bases of the benzidine type have been prepared, 

 various groups — CHj— , — CHjS— , — CH,SCHj— , 

 etc., being introduced between the two rings. In 

 particular bases have been made from mustard 

 gas which are readily converted into azo dyes. 

 The whole work is a study of constitution and 

 color. 



The reaction of propylene, butylene, and amy- 



