August 7, 1908] 



SCIENCE 



189 



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Bea/rrangements in the Camphor Series: the 

 Structure of Laurolene: W. A. Notes and C. 

 G. Debeick. 



An attempt is being made to gain a better 

 insight into the nature and cause of some of the 

 puzzling rearrangements which occur so fre- 

 quently among the derivatives of camphor. The 

 oxidation of laurolene, CsHi4, has given a diketone, 

 CsHuO.. It seems almost certain that this ketone 

 must contain two groups of the structure CH3CO. 

 The melting point of its disemicarbazone indicates 

 that it is not 2, 7-octanedione, which would be 

 formed if laurolene were tetrahydro-ortho-xylene. 

 The activity of laurolene also excludes that for- 

 mula. The formula of Eykmann, according to 

 which laurolene is 1, 2, 3-trimethylcyclopentene, 

 is now the most probable. 



Studies in Nitration, VI. Melting Points of Mix- 

 tures of Ortho- and Paranitraniline : J. Bishop 

 Tingle and H. F. Eolkeh. 



The authors have shown previously that the 

 melting points of mixtures of o- and m- and of 

 m- and p-nitranilines form regular curves, where- 

 as the mixtures of o- and p-nitraniline melted at 

 highly irregular temperatures. A fresh series of 

 mixtures of these two isomers has been prepared 

 with additional precautions to secure homogeneity 

 and also constancy of composition. The m.p. 

 of each mixture was determined, the material was 

 allowed to solidify and it was then melted once 

 more. The results have been plotted in the form 

 of two curves which do not exhibit a very simple 

 relationship and which are both highly irregular. 

 Moreover, the melting points of mixtures of the 

 o- and p-nitranilines are not nearly so sharp as 

 those mixtures of the other isomers. Suggestions 

 were made as to the possible cause of these phe- 

 nomena which are probably due to polymorphism. 



Action of Sodium on Certain Esters: J. Bishop 



Tingle and Eenest E. Goksline. 



According to Claisen's hypothesis, which was 

 adopted subsequently by Nef, the formation of 

 ethyl acetoacetate, CHsOCOH) :CHGOAH„ from 



ethyl acetate, CHjCOX'^Hs, depends upon the pre- 

 vious production of sodium ethylate, which is the 

 active agent in producing the condensation. A. 

 Michael, on the other hand, considers that sodium 

 reacts directly with ethyl acetate, forming such 

 a compound as NaCH,C0,C,H5 or CH,:C(ONa)- 

 CO2C2HB. We have purified ethyl acetate with 

 great care by a new method and find that the 

 specimens obtained in this way react very readily 

 with sodium, either alone or in the presence of 

 ether. Experiments have been carried out on the 

 interaction of sodium and certain esters. It is 

 found that ethyl malonate, H,C{CO,CjHj), ethyl 

 chlormalonate, CHCOjCjHb), and ethyl dimethyl- 

 malonate, ( CH3 ) jC ( C0,C,H5 ) , react with 2, 1 and 

 4 atomic proportions of sodium, respectively. 

 Ethyl phthalate and the metal react, but an in- 

 soluble coating is formed over the surface of the 

 wire so that the action quickly ceases. Our study 

 of the catalytic effect of ether, pyridine and 

 quinoline in promoting the Claisen reaction 

 (acetoacetie ester condensation) has been ex- 

 tended. The results of our work support 

 Michael's explanation of the reaction and show 

 that the Claisen-Nef hypothesis is open to the 

 gravest doubt. 



Intramolecular Rearrangement in the Phthal- 

 amidio Acid Series: J. Bishop Tingle and H. 



F. ROLKEE. 



In conjunction with Messrs. Cram and Love- 

 lace, the senior author has sho-wn previously that 

 phthanilie acid, CeH^NHCOCeH^COnH, changes 

 very readily in the presence of amines to phthal- 

 anil, 



/CO. 

 CeH/ >NH. 



It was suggested that the change in the equa- 

 tion was preceded by the formation of a salt, 

 CoHNHCOCeHiCOiNHsR. This hypothesis has 

 been confirmed by the preparation of several such 

 salts, the stability of which is found to vary 

 according to the nature of the amine and 

 also to that of the group R in the parent acid 

 RNHCeH4C02H. In addition to this reaction a 

 second one occurs which consists in the replace- 

 ment of the group R in the original acid by a 

 different complex R' derived from the amine thus, 

 RNHCsH,CO,H + R'NH,, R'NHCeH.CO, + RNH,. 

 This new acid may then pass into the imide 

 ( anil ) . Finally there is evidence showing that 

 occasionally some diamide, CoHj ( CONHR ) ;, may 

 be formed. The reactions have been studied in 

 detail with a considerable number of acids and 



