Seftembeb 3, 1909] 



SCIENCE 



319 



C„H, 





COsCH, 

 CO,CH,' 



which by PjOj is converted into an oil, 

 ^CO=CH, 



C,H5N=C 



< 



COjCH, 



This methyl phenyliminomalonate is a remarkable 

 reaction substance, an analogue of phenyl iso- 

 cyanate. The reactions of this, and analogous 

 compounds in this series, are being investigated. 

 HCl and HBr appear to jidd on the carbonyl 

 group of ethyl oxomalonate, but owing to the low 

 temperature {below — 30°) at which the crys- 

 talline products dissociate we have not been able 

 to get true analytical figures as we have done 

 with methyl oxomalonate and these acids, where 

 one molecule of the acid is added to the keto ester. 



Hydrogen Polysulphide as a Reducing Agent: 



Alfred Tingle. 



The hydrogen polysulphide, or mixture of poly- 

 sulphides, prepared by boiling lime with flowers 

 of sulphur and acidifying the resulting cooled, 

 clear liquid, possesses the following advantages 

 as a reducing agent. It is neutral; it is readily 

 soluble in ionizing media, such as water or alco- 

 hol, and also in non-ionizing liquids, such as 

 carbon disulphide. The exact concentration of 

 these solutions may be determined easily and 

 with a high degree of accuracy by titration with 

 iodine solution. Preliminary experiments on the 

 reducing power of the polysulphide show that its 

 reaction with nitrobenzene is vigorous, but rather 

 complicated. Picric acid is easily reduced, at the 

 ordinary temperature, to picramic acid. The work 

 is being continued at the McMaster University. 



Intramolecular Rearrangement of Phthalamidio 

 Acids: J. Bishop Tingle and B. F. Pablett 

 Bbentoit. 



In continuation of the work of Bishop Tingle 

 and Rolker' on the interaction of amines and 

 phthalamidic acids, RR'NCOC.H^COjH, the au- 

 thors have studied the action of pyridine, aniline 

 and j3-naphthylamine, respectively, on phthaldi- 

 phenylamidie, phthnl-p-chlorphenylamidic and 

 phthaldiisobutylamidic acids. An investigation 

 has been made of the behavior of benzylamine 

 with phthal-ptolylamidic and with phthal-m- 

 nitrophenylamidic acids; this latter acid has also 

 been caused to react with the following additional 



V. Am. Chem. Soc, 30, 1882. 



bases: alcoholic ammonia, diisoamylamine, benzyl- 

 ethylamine, dibenzylamine, isoamylamine, butyl- 

 amine, isobutylamine and tribenzylamine. The 

 results are in general accord with the conclusions 

 reached by Bishop Tingle and Rolker. Consider- 

 ing, for the sake of illustration, primary amines, 

 RNHj, and monosubstituted phthalamidic acids, 

 RNHCOCcH^COjH, one or more of the following 

 four products are formed: 



CO. CO 



C.H./ >NR, C„H.< >NR', 



\co/ \co/ 



RNHCOCH^CONHR' and C„H.(C0NHR):. 



Action of Amines on Dicarboxylic Acids of the 

 Alipliatic and Aromatic Series: J.. Bishop 

 Tingle and B. F. Pablett Bbenton. 

 The work of Bishop Tingle with Messrs. Rolker 

 and Brenton (cf. preceding abstract) has shown 

 that, under certain conditions, the chief product 

 of the interaction of amines, RNHj, on phthal- 

 amidic acids, R'NHCOCcH.COjH, is an imide. 



c,: 



CO 



\co/ 



NR' or CcH./ <NR. 



\co\ 



Occasionally, however, the unsymmetrical or the 

 symmetrical diamide, R'NHCOC„H,CONHR, or 

 C<,H,(CONHR'),, is also formed. Bishop Tingle 

 and Bates (of. following abstract) have found 

 that, under suitable conditions, the diamide is the 

 chief material from amines and dicarboxylic acids 

 of the aliphatic series. Few if any of the unsym- 

 metrical diamides are known. A study has been 

 made, therefore, of the action of a variety of 

 amines on phthalic acid, in the hope that, by selec- 

 tion of suitable experimental conditions and also 

 of the groups R and R" in the amine, RR"NH 

 (R and R"^ hydrogen, alkyl, or aryl), a method 

 might be developed for the preparation of unsym- 

 metrical amides. The authors have obtained sev- 

 eral of the compounds in question and have pre- 

 pared, in the course of the work, a considerable 

 number of new substances of other types which 

 will be described in due course. 

 Aliphatic Phenylamidio (Anilic) Acids: J. 



Bishop Tingle and S. J. Bates. 



It has been shown by Bishop Tingle and his 

 co-workers that certain amidic acids of the 

 phthalic series, R>rHCOC,H,COjH, form salts with 

 amines and that these salts quickly undergo con- 

 densation to the imide, 



/COv 

 C.H.< >NR. 



\co/ 



