- 138 - 



correctness of Semmler's sabinene formula 1 ), but also for the formula 

 given for the terpinene hydrohalogen addition products: 



CH 2 CH 3 



II I 



C CC1 



| X 



CH 2 

 1 



+ '< 



2HC1 







H 9 C CH 2 



1 1 



H C CH 



C 



| 









H C CH 2 



CC1 



1 



CH(CH 3 ) 2 









CH(CH 3 ) 2 



sabii 



lene 







terp 



inene dihydrochloride 



Contrary to Semmler 2 ), Wallach was able to convert sabinene 

 readily by treatment with dilute sulphuric acid (1:7) into terpinene, 

 which was identified by the nitrosite and the dihydrochloride. 



On account of the relationship between thujene and sabinene, the 

 former was also submitted to examination, and contrary to the results 

 obtained by Kondakow 3 ) and Tschugaeff 4 ) Wallach has found 

 that also from thujene, by treatment with hydrohalogen acids, not 

 dipentene, but compounds of terpinene hydrohalogenide are formed: 



C H„ C H„ 



CC1 



HC X 



| X 



CH 



1 



+ 



2HC1 



H 2 C CH, 



1 1 



H 2 C 



C 



CH 2 







H C C H 9 



CC1 



1 



CH(CH 3 ) 2 







CH(CH 3 ) 2 



a- till 



ijene 







terpinene dihydrochloride 



These examinations of Wallach render the thujene formula accepted 

 by Kondakow illusory. 



Semmler 5 ) also expresses himself on the relationship of sabinene 

 and thujene towards terpinene. The conversion of sabinene in terpinene 



*) Comp. Report October 1902, 91. 



2 ) Semmler, Die atherischen Ole, vol. II, 289. 



8 ) Chem. Ztg. 26 (1902), 722. 



4 ) Berl. Berichte 37 (1904), 1483. 



5 ) Berl. Berichte 39 (1906), 4416. 



