Dr. Hofmann and M. Cahours on a New Class of Alcohols. 227 



Sulphide of Alhjle (Garlic Oil), Cj2 Hjq S^. — When iodide of 

 allyle is allowed to fall drop by drop into a couceutrated alcoholic 

 solution of protosulphide of potassium, a very energetic action ensues, 

 the liquid becomes very hot, and an abundant crystalline deposit 

 takes place of Iodide of potassium. It is important that the iodide 

 of allyle should only be added gradually to avoid spirting, by which a 

 part of the product would be lost. As soon as the action ceases, 

 the liquid Is mixed with a slight excess of sulphide of potassium ; 

 addition of water now separates a light yellowish limpid oil possess- 

 ing a strong smell of garlic. When rectified, this liquid becomes 

 colourless. It bolls at 140° C, and gives with nitrate of silver a crystal- 

 line precipitate soluble In a boiling mixture of alcohol and water, 

 and separating from this solvent In the form of beautiful white 

 needles, absolutely Identical with those which the natural essence of 

 garlic produces. Sulphide of allyle also comports Itself with corrosive 

 sublimate and with bichloride of platinum exactly like the natural 

 garlic oil. 



AUijIe-Mercaptan, Cg Hg 83. — When In the process for the prepa- 

 ration of the preceding compound the protosulphide of potassium Is 

 replaced by the hydrosulphate of sulphide of potassium, a volatile 

 product is obtained, having a similar but more ethereal odour. This 

 substance acts with energy upon protoxide of mercury, with which it 

 forms a compound, dissolving in boiling alcohol, and separating from 

 it on cooling In the form of pearly scales of remarkable brilliancy, 

 which present the greatest resemblance to the mercaptlde of mercury. 

 The liquid obtained in the above-mentioned reaction bolls at 90°, 

 and possesses a composition and an aggregate of properties which 

 closely resemble those of the mercaptan of the ethyle-s?rles, being, in 

 fact, the allyllc mercaptan, Cg Hg Sj. 



Alhjlumine, Cgll^N. — By boiling cyanate of allyle (Cg Hj NO2) 

 with a concentrated solution of caustic potassa until the oily layer 

 entirely disappears, a complete decomposition ensues, and the residue 

 contains only a mixture of carbonate of potassium with an excess of 

 the alkaline hydrate ; the volatile products condensed In hydrochloric 

 acid furnish a saline mass which may be obtained crystalline on 

 evaporation. This substance is always a mixture, tha constituents of 

 which vary both in nature and properties. The action of potassa on 

 it not only separates a base, which Is readily soluble in water, but 

 also InsoIul)le basic oils, the boiling-point of which rises to 180° C. 

 Simple distillation of the liberated bases appears to give rise to de- 

 compositions, and thus to Induce further complication. We have 

 not succeeded in ascertaining with perfect precision the nature of 

 this mixture, but we have found that It Invariably contains a con- 

 siderable quantity of a base which bears the same relation to allylic 

 alcohol that Is observed between ethylamlne and ordinary alcohol. 

 The formation of this substance, which we propose to designate 

 nllylaniine, Cg II7 N, is perfectly analogous to the production of 

 etliylamine by means of cyanate of ethyle. 



Dialhjlaminc, C,., II,jN. — Im])urc allylaminc, obtained by the 

 action of potassa on the cyanate, when digested with a second quau- 



Q2 



