54 



SCIENCE 



[Vol. LVI, No. 1437 



activity of this diazo compound with the Lewis- 

 I/Angmuir theory of the combination of atoms in 

 ' ' non-polar ' ' compounds. 



Further observations on the nitration of halo- 

 genated phenols: L. Chas. Eaipord and Liang 

 Ti Ho. Previous work by Raiford and Heyl has 

 shown that the method of nitration of brominated 

 phenols first used by Zincke is suitable for the 

 bromine and iodine compounds, but that the nitro 

 radical fails to replace chlorine; and that, fur- 

 ther, both dibrominated and tribrominated deriva- 

 tives of ortho and meta cresols may be expected 

 to give isomeric nitro derivatives. The small 

 yield (10-12 per cent.) of the para siomeride, 

 3-bromo-5-nitro-o-cresol, obtained when dibromo- 

 o-cresol was nitrated in this way raised the ques- 

 tion as to whether the position taken by the nitro 

 radical depends more upon the relative position 

 of the halogen atom or upon its character. To 

 get data on this point, 3-chloro-o-bromo-o-cresol 

 and its isomer, 3-bromo-5-ehloro-o-cresol, were 

 nitrated. In each case the bromine was displaced, 

 giving the isomeric compounds, 3-<?hloro-5-nitro-o- 

 cresol and 3-uitro-5-c!iloro-o-eresol. 



New organic selenium compounds: Makston 

 Taylor Bogert and Y. G. Chen-. By the action 

 of hydrogen selenide upon acyl anthraniUc nitriles, 

 selenoquinazolones have been prepared and 

 studied. Derivatives of 2-phenyl benzselenazole 

 also have been investigated and show some inter- 

 esting properties. 



The synthesis of a tMazole analog of oinchophen 

 (atphan) : Marston Taylor Bogeet and E. 

 Abrahamson. 2-phenyl benzothiazole is nitrated, 

 giving the 6-nitro derivative, which is reduced to 

 the amine, and the latter is then changed to the 

 corresponding carboxyl compound through the 

 diazo reaction. Various derivatives and collateral 

 compounds were prepared. The position of the 

 nitro group was proved by decomposition of the 

 amine and by its conversion to the- benzobis 

 thiazole. 



Sydrocyanie acid: an ammono carhonous acid 

 and an aynmono formaldehyde: Edward C. Frank- 

 lin-. From a purely formal point of view HNC 

 represents hydrocyanic acid as an ammono car- 

 bonous acid, while the nitrile formula represents 

 it simultaneously as an ammono formaldehyde and 

 as formic ammonid. Sodium ammono carbonite 

 may be nitridized to an ammono carbonate by a 

 considerable number of methods, as, for example, 

 by the action of sodium ammono nitrate and of 

 cj-anogen as represented- by the equations, 

 NaNC + NaNa = NCNNa, + N"^ and 



NaNC + C,N^ = NaNCCN)^ -(-. C. As an am- 

 mono aldehyde, hydrocyanic acid undergoes poly- 

 merization and condensation, forms addition com- 

 pounds with bisuMtes, ammonia, water and alco- 

 hol, reacts -with hydrosylamine, hydrazine and 

 phenylhydrazine, and is reducible to an ammono 

 alcohol. 



A study of the optimum condition for the 

 formation of the Grignard reagent: Henry Gil- 

 man and Chas. H. Meyers. Two satisfactory 

 methods for the estimation of the Grignard re- 

 agent are being used. One involves titration with 

 standard acid and the other the measurement of 

 gas evolved when the reagent is decomposed by 

 water. The study concerns those ordinary factors 

 affecting the yield: rate of addition of BX, con- 

 centration of reagents, kind of magnesium, cool- 

 ing during formation, refluxing after formation, 

 stirring, kind of air protection (calcium chloride, 

 soda lime, etc.), catalysts, etc. This preliminary 

 report is on ethyl magnesium iodide. 



The reaction between thi-onyl ajiiline and the 

 Grignard reagent: Henry Gilman and Harry Ij. 

 Morris. In connection with a series of studies 

 on the mode of reaction of the Grignard reagent 

 with compounds ha-ving more than one reactive 

 grouping, thionyl aniline (C.H.N— S=0) has 

 been treated -with several EMgX compounds. 

 Phenyl magnesium bromide gives a good yield of 

 the anilide of beuezen sulfinic acid. Excess of 

 the Grignard reagent gives the same compound. 

 Up to the present no success has attended attempts 

 to determine the mechanism of the reaction — the 

 — MgX may have added either to the nitrogen or 

 to the ox3'gen. 



Arsenated heterocyclic compounds prepared 

 from 3, 4-diaminophenyl arsonic acid (amino 

 arsanilic acid) : W. Lee Le-wis and E. S. Bly. 

 The great reacti-vity of the ortho-diamines with a 

 great variety of substances yielding quinoxalines, 

 azimides, piafthioles, imidazoles, etc., suggested 

 the easily available amino arsanilic acid as a 

 fruitful starting point for new organic arsenicals. 

 3,4-diaminophenyl arsonic acid is made by nitra- 

 ting oxalyl p-arsanilic acid and reducing the nitro 

 compound with ferrous chloride and ammonia. 

 Thus far this compound has been condensed -with 

 benzil, oxalic acid, pyruvic acid, maltosone yield- 

 ing the following: 2,3-diphenyl-quinoxaline-6- 

 arsonie acid, 2, 3-diketoquinoxaline-6-arsonic acid, 

 2-methyl-3-hydroxy-quinoxaline-6-arsonic acid, and 

 3- (glucosido-erythrityl) -quinoxaline-6-arsoiiic acid. 



Derivatives of the heta-chloro-vinyl arsines: 

 W. Lee Le-w-is and H. W. Stiegler. The chloro- 



