II. 



NEP. — NITliOPAKAPFlNE 8ALTS. 147 



CHa-C = NOAg + ICHs 

 I II 

 ^O^ o 



CHs I CH3. /NO2 



= CH3-C-N0Ag= C + Agl. 



I II CH3/ ^NOa 



NO2O 

 Addition Product. 



There are now so many cases known, where, by the interaction of 

 silver salts with alkyliodides or acid chlorides, no direct or only par- 

 tially a direct replacement of the silver takes place,* that this explana- 

 tion is not at all improbable, — especially also when one considers the 

 remarkable behavior of silver fulminate towards hydrogen sulphide 

 and towards hydrochloric acid (see following paper). 



The formation of formic aldehyde, ethylnitrolic acid, dinitroethane, 

 /:? dinitropropane and of a fifth compound, probably ethylnitrolic acid 

 methylester, on treating silver dinitroethane with iodide of methyl, is 

 therefore perfectly cleared up by the above considerations. 



IV. The Action of Acid Chlorides on Nitroparaffine 



Salts. 



The former experiments on the action of acetylchloride and of 

 benzoylchloride on sodic nitromethane and on sodic nitroethane t 

 have led to no positive results. Kissel has shown J that in these 

 reactions some dibenzhydroxamic acid and diacethydroxamic acid is 

 formed, but these can only have been formed, however, by a complete 

 destruction of the nitroparaffine molecule. 



I have also carried out many fruitless experiments on these salts 

 with acetylchloride and benzoylchloride, and also with chlorocarbonic 

 ether; both neutral and acid products are formed, which cannot be so- 

 lidified, and which do not distil under reduced pressure without decom- 

 position. Entirely analogous results were obtained by the action of 

 acetylchloride and benzoylchloride on nitroethane-mercuric-chloride, 



* Ann. Chem. (Liebig), CCLXX. 329, 331 ; CCLXXVI. 232 ; (TLXXVII. 

 73 Tlie experiment with silver afet3'lacetone lias been carried out here by 

 Dr. Curtis8 witli larger quantities of material, and both products have been 

 analyzed. 



t V Meyer and Rilliet, Ber. d. chem. Ges., V. 1030; VI. 1168. 



t Ber. d. cliem. Ges., XV. Ref. 727 and 1574. 



