98 PROCEEDINGS OF THE AMERICAN ACADEMY. 



was obtained after the second precipitation 50 grams of a dark-colored 

 oil that collected after continued distillation in vacuo, nearly colorless, 

 for the most part at l98°-202°. Under atmospheric pressure this oil 

 distilled with some decomposition at 290°-295°, specific gravity at 20°, 

 0.9235. The values obtained by analysis corresponded to the formula 

 Ci 8 H 86 S. 



I. 0.2005 gram of the oil gave 0.5602 gram C0 2 , and 0.2214 gram H 2 0. 

 II. 0.1937 gram of the oil gave 0.1634 gram BaS0 4 . 

 III. 0.2011 gram of the oil gave 0.1636 gram BaS0 4 . 



Calculated for Found. 



C 18 H 3G S. I II. IIL 



C 76.06 76.22 



H 12.67 12.35 



S 11.27 11.57 11.18 



We have made no attempts toward the separation of sulphur com- 

 pounds with higher molecular weights, but there is no doubt that higher 

 homologues are contained in the less volatile distillates which we have 

 separated from the original oil. It is probable that intermediary mem- 

 bers of this series are contained in the distillates examined, and that they 

 might he identified in larger quantities of material. 



As has been shown in the method of preparation, the thiophanes com- 

 bine readily with alcoholic mercuric chloride to form viscous oils. They 

 also form addition products with chlorplatinic acid, which are heavy 

 viscous oils. When heated in a sealed tube with ethyl iodide, addition 

 products are formed which crystallize in small prisms, — C n H 2n S, C 2 H 5 I. 

 These addition products form alkaline hydrates when warmed with 

 silver oxide and water : 



\/ \/ 



S — C 2 H 5 S — C 2 H 5 



X I X OH 



Bromine exerts a characteristic action on these sulphur compounds. 

 Immediately when they come in contact, combination follows with al- 

 most explosive violence, and copious evolution of hydrobromic acid in 

 equivalent amounts to the bromine added. It is wholly unlike the 

 behavior of unsaturated hydrocarbons with bromine. Probably part of 

 the bromine combines with the sulphur, but the evolution of hydrobromic 

 acid begins immediately, doubtless due to the ready replacement of 

 the methylene hydrogen atoms. 



