■n2 REPORT— 1900. 



Moreover, dihydroisolauronic acid when warmed with dilute sodium 

 liypobromite is converted into a tribasic acid, C,,H].,Ofj, which loses carbon 

 dioxide wlien heated, yielding aa-dimethyladipic acid. 



,CMeo.CO CMeo.COOH CMe^-COOH 



CH2 CH., -> CH„ COOH -> CH^ +C0., 



^CH.,-CH.COOH ^CHa— CH.COOH \CH2-CH2.COOH 



Diliydroisolauronic Acid. Intermediate I'roduct. oa-Dimethyladipic Acid.' 



(ii.) Electrolysis of AWo-Ethyl Hydrogen Camphorate. — When this 

 ester is electrolysed it yields a mixture of esters, chief amongst which is 

 that of (a) aWo-campholytic acid, a /3y-unsaturated acid, as it readily 

 affords campholactone on treatment with acids : it is pi'obably stereo - 

 isomeric with lauronolic acid,^ and (b) of camphononic acid produced by 

 the superposition of electrolysis and oxidation. 



The constitution of lauronolic acid and rt?^o-campholytic acid has not 

 been determined, but one must assign to camphononic acid one of the 

 following two formula,' 



""in 



CO . CMe2. CHo . CMeo. 



! CMe.COOH or ' ^^CMe.COOH 



OH,-CH, CO-CH2 



as it is readily obtained by the mere action of heat on the open chain 

 tricarboxylic acid, homocamphoronic acid, and must therefore be a penta- 

 methylene and not a tetramethylene derivative ; for since it affords 

 camphoronic acid (F. 1. a. ii.) on oxidation it could only be one of these.^ 

 It should be pointed out that the first of the two formulse above given 

 is almost certainly the correct one, as camphononic acid does not at once 

 atford an oxime or hydrozones as do the majority of acids having the 

 carbonyl group in attachment to two CHo groups. Moreover it cannot be 

 made to combine with hydrogen cyanide, and it is therefore highly pro- 

 bable that the reactivity of the carbonyl group is affected by its attach- 

 ment to a carbon atom on which no hydrogen is present.' 



(b) Action of Alumhuum Chloride a7id of S/dphuric Acid 

 on Camphoric Anltijdvidc. 



AViien camphoric anhydride is brought into contact with aluminium 

 chloride in chloroform solution it loses carbon monoxide and yields cliiefly 

 isolauronolic acid.'' A third inetliod of obtaining isolauronolic acid is 

 supplied by the following series of changes. Camphoric acid when 

 warmed with sulphuric acid yields sulphocamphylic acid by loss of the 

 elements of formic acid and addition of the elements of sulphuric acid. 



* Compare Bouveault, Bull. Soc. Chim. (iii.), 17, 1)99, and 19, 462 ; and Blanc, 

 Bvll. Soc. Chim. (iii ), 19, 277, 350, 533, and C99; 21, 830 ; and 23, 107 and 273 ; and 

 Perkin, Trans. Chem. Soc, 73, 796. 



- Walker, Trans. Cham. Soc, 69, 748. 



■' Comimre Bredt and Rosenberg, Aouialen, 1896, 289, 13 ; Wislicenus, Hid., 

 275, 309 ; and Perkin and Crossley, Trans. Chem. Soc, 73, C. 



' See Lapworth and Chapman, Trans. Cliein. Soc, 76, 989, and 77, 446, and Lap- 

 wortb, Ihid., 75, 1134. 



■■' Blanc, BiiU. Soc. Chim. [iii.]. 15, 1191. 



