- 8 7 - 



unsaturated, bicyclic hydrocarbon C i0 H L6 , nor-bicyclo ecsantalane 

 (b. p. 62 to 64 at 9 mm. pressure; 186 to 189 at 760 mm. pressure; 

 d2o° 0,8827; n D 1,4779; molecular refraction found 43,59, calculated 

 for C t0 H d i e / = 43,52). 



When heating santalol with alcoholic potash in a sealed tube 

 to 160 , an alcohol C 11 H 18 was formed (d 2 oo 0,9738; n D 1,495) 

 which could be oxidised into the aldehyde C 11 H 16 0. The inversion 

 of santalol by means of hydrochloric acid or glacial acetic acid and 

 sulphuric acid, did not lead to uniform results, but Semmler and 

 Bode believe from the rise in the refractive index of the strongly 

 laevorotatory products obtained, to be justified in concluding that a 

 disruption of the tricyclic santalol has taken place. 



From the chlorinated methyl ester of tricyclo ecsantalic acid (see above) 

 there was obtained by reduction with sodium and alcohol, dihydrobicyclo 

 ecsantalic acid C u H 18 2 (m. p. 58 ) and from the ester of this acid, 

 in the same manner, dihydro bicyclo ecsantalol C u H 20 O (b. p. 128 

 to 133 at 10 mm. pressure; d2o° 0,9724; n D 1,492). 



The determination of the molecular refraction of the tricyclic and 

 bicyclic bodies described, resulted in so far in anomalies, that the 

 calculated molecular refraction was exceeded by the one found. As 

 in the bicyclic systems of tanacetone and sabinene also abnormal 

 (i. e. too high) molecular refractions were found, to which Wallach 1 ) 

 in the case of the latter has particularly called attention, Semmler 2 ) 

 assumes that to such systems an increment is due, which is smaller than 

 that of a double-bond (1,7), and should further be taken into account 

 when calculating the molecular refraction. In the tri- 

 cyclic systems this can be still larger than in the bicyclic. 



With regard to the constitution of santalol and its 

 derivatives, Semmler could not yet say anything definite, but 

 he hopes to be able to decide by further experiments, 

 whether a naphthalene ring with a bridge-bond, analogous to that of 

 anthracene, belongs to them or whether they are based upon another system. 



The first runnings of sandalwood oil had long ago been examined 

 in detail by v. Soden and Miiller 3 ), and also by Guerbet 4 ), and the 

 presence in them of santene C 9 H 14 , a ketone C 10 H 16 O, sesquiterpenes 

 C 15 H 24 , and also teresantalic acid C 10 H 14 O 2 had been established. 

 The last-named body has recently been the subject of an examination 



*) Liebig's Annalen 347 (1906), 319; Berl. Berichte 40 (1907), 585; Report 

 April 1907, 140. 



2 ) Berl. Berichte 40 (1907), 1120. 



3 ) Pharm. Ztg. 44 (1899), 258; Arch, der Pharm. 238 (1900), 353 and 367; 

 Report October 1900. 59. 



4 ) Compt. rend. 130 (1900), 417 and 1324; Report April 1900, 42 and October 

 1900, 58. 



