— i3i — 



ethereal solution with potash powder, there are formed intermediarily, 

 by substitution of the iodine atom by OH and loss of water, oxides 



R.C(CH 3 ).CH 2 



which on distillation at atmospheric pressure converted into are hydra- 

 tropic aldehydes R • CH (CH 3 ) • CHO. But if the hydriodic acid is 

 split off with silver nitrate or mercuric oxide, there occurs, as already 

 previously observed, a very remarkable migration of the carbon linkings, 

 with formation of /^-ketones, that is to say, formation of a normal side- 

 chain: — Hi 



R. C(OH)(CH 3 ) • CH 2 I -> R-CH 2 -CO • CH 3 . 



In this manner were produced from y-anethol ^-anise ketone, from 

 ip-a\\y\ phenetol p-ethoxy phenyl acetone, from y-safrol methylene 

 dioxyphenyl acetone, and from ^-methyl eugenol dimethoxyphenyl 

 acetone, and the two last-named were identified by means of the semi- 

 carbazones with the products obtained in another way by Walla ch 

 and by Hoering. 



Accordingto Fourneau and Tiffeneau 1 ) substituted ethylene 



oxides of the benzene series behave differently, according to the 



position of the substitute when they are rearranged by the application 



of heat. The authors differentiate between monosubstituted oxides 



R • C H 2 • CH • C H 2 , 



symmetricallyl disubstituted 



R. CH . CH- CH 3 , 



V 



and asymmetrically disubstituted oxides 



R • C(CH 3 ) • CH 2 



\o/ 



The first-named oxides, such as the oxides derived from allyl- 

 benzene, estragol, safrol, and methyl eugenol, which pass over without 

 decomposition at reduced pressure, are converted by distillation at 

 ordinary pressure in substituted hydrocinnamic aldehydes, 

 R • CH 2 . CH 2 • CHO, which were identified by the melting points 

 of their semicarbazones. 



The symmetrically disubstituted oxides are converted into 

 /? -ketones of the formula R • CH 2 • CO • CH 3 ; there was, for instance, 

 obtained from phenyl propenyl oxide 



QH '- CH • CH • CH 3 



\o/ 



*) Compt. rend. 141 (1905), 662. Comp. ibid. 140 (1905), 545. Report 

 October 1905, 118. 



