— rig — 



the other hand the opinion held by Semmler 1 ) on the structure of 

 isomeric fenchyl alcohols and fenchone. After introductory historical 

 observations on the constitution of bornyl alcohols, the author attacks 

 Bredt's view according to which borneol and isoborneol must be 

 looked upon as secondary alcohols, stereo isomeric with each other. 

 But — Kondakow thinks — so long as the conditions prevailing 

 in the conversion of borneol, and especially of isoborneol, into bornylene 

 or camphene respectively, have not been elucidated with unobjectionable 

 uniform material, and the identity of the two isoborneols originating 

 from camphene and from camphor has not been proved, no further 

 conclusions on the constitution of these alcohols should be drawn. 

 On the strength of the present experimental material, Kondakow 

 wishes in the first place to emphasize the tertiary character of iso- 

 borneol. 



With regard to the remarks made by the author on an isoborneol 

 preparation originating from our factory, which Biltz had examined 

 for its cryoscopic behaviour, we wish, however, to reply that it would 

 only have been necessary for Mr. Kondakow to address himself 

 personally to us, if the question of the production of our isoborneol 

 had interested him for his studies. We would then, of course, have 

 been glad to inform him that the preparation in question had been 

 produced by the universally known method, by means of glacial acetic 

 acid and sulphuric acid from the camphene of citronella oil. 



Kondakow further expresses himself in disagreement with S em ru- 

 ler's 2 ) new fenchone formula. The oxidation-result (formation of 

 isocamphoronic acid and dimethyltricarballylic acid) is, if a re-arrange- 

 ment is accepted, explained equally well in Wallach's fenchone formula. 

 Semmler's view on the formation of m-cymene from fenchone seems 

 to Kondakow somewhat far-fetched, and one-sided. The conclusions 

 which Semmler, by comparing the physical properties of camphor 

 and fenchocamphorone on the one hand, and fenchone and cam- 

 phenilone on the other, draws on the constitution of these bodies, 

 appear to Kondakow somewhat risky, in view of the present inadequate 

 observation-material. With regard to the detailed discussion on the 

 constitution of the haloid anhydrides and fenchenes from the two 

 fenchyl alcohols, into which Kondakow enters at the end of his work, 

 and which is chiefly of a purely hypothetical character, we need here 

 not go further into. 



It is a well known fact that the esterification of sensitive and 

 especially of tertiary alcohols is accompanied by great difficulties. 



x ) Chem.-Ztg. 29 (1905), 1313; Report April 1906, 124. 

 2 ) loc. cit. 



