— 196 — 



hydroxycamphenilane- (camphenilol) di- car boxy lie acid 

 lactone X, m. p. 230 , and of the calcium and barium salts of 

 the latter. 



The reduction of the /J-hydrobromo bornylene carboxylic acid with 

 potassium-amalgam led, as a result of the ready displacement of the 

 bromine-atom by hydrogen, to ortho - camphane carboxylic 

 acid XI, m. p. 90 to 91 , b. p. (13 mm.) 153 . But similar treatment 

 of the a-brominated acid yielded the same hydroxy -acid which had 

 been formed during the treatment with alkali carbonate; it therefore 

 underwent no reduction. On the other hand, reduction with zinc and 

 hydrochloric acid in glacial acetic acid solution yielded an acid free 

 from bromine, m. p. 209 . This acid, which has not been further 

 investigated up to the present, may be surmised to be the hydrated 

 acid which was looked for. 



The object of the examination of the bornylene XII, formed by 

 treating /J-bornylene carboxylic acid with alkali, was to determine the 

 uniform character of this terpene. This body, which is of quite 

 exceptional volatility and passes over quite easily even with ether- vapour, 

 was found to possess the following constants: m. p. 113 , b. p. 146 

 at 740 mm., M D in methyl alcohol — 26,96°, in toluene — 21,69°. 

 Hence the dextro-rotatory testing material had yielded a body of the 

 opposite rotation, a circumstance of which other examples were already 

 on record. Judging by its high m. p. the bornylene thus obtained 

 was considerably purer than the terpene prepared from bornyl iodide 

 by Wagner and Brickner, which had m. p. 97°, and also than the 

 terpene obtained by Tchugaeff from bornyl xanthogenate, which 

 melted at 103 to 104°. The body from bornyl iodide may perhaps 

 contain not inconsiderable proportions of camphene, which can only 

 be separated imperfectly from each other by means of hydration 

 according to Bertram -Walbaum's process (by this method bornylene 

 yields an alcohol termed by Wagner /?-borneol, m. p. 203 to 204°). 

 Tchugaeff s terpene was rather less impure, and was converted into 

 camphoric acid, m. p. 186°, by oxidation with a 1 °/o aqueous 

 solution of permanganate. 



In a further paper Bredt and Sandkuhl 1 ) deal with the relations 

 of the camphyl glycols to the borneol carboxylic acids; a subject 

 which has also been touched upon in the previous communication. The 

 method of preparing the alleged inseparable mixture of m- and m- 

 £rans-camphyl-grycol XIII was improved, as was also the method of 

 obtaining the primery material (hydroxy-methylene camphor), and for 

 the separation of both stereomeric modifications fractional crystallisation 

 from acetic ester was employed. The m-glycol, from which water 



*) Liebig's Annalen 366 (1909), 62; see also Report October 1906, 135. 



