371 



solution of potassium hydroxide and meiy be readilj^ identified as 

 methyl nitrite. The presence of nitromethane cannot be demonstrated 

 amongst the reaction products. 



In an experiment made with 1 gram of nitramine and 5 c.c. of 

 methyl alcohol 60.6 c.c. of methyl nitrite (reduced to 0° and 760 mm.) 

 were collected in 4 hours (Theory 67.5 cc). 



The methyl ester of trinitromethylnitraminophenol formed in the 

 reaction has been described previously (I.e.). 



Interaction of ethyl alcohol likewise gives ethyl nitrite without 

 formation of nitroethane. The ethyl ester of phenol has already been 

 described. 



With dry propyl alcohol is formed the propyl ester, melting at 

 118°, also propyl nitrite boiling at 57°. Nitropropane is not formed. 



Zwbutyl alcohol on heating with the nitramine (in the water-bath) 

 gives the isohwiy\ ester melting at 95° and /.wbutyl nitrite boiling 

 at 65°. 



Fermentation amyl alcohol likewise yielded amyl nitrite and an 

 amyl ester melting at 83°. With this alcohol the mass was coloured 

 darker than with the other alcohols. It also appea»-ed that more free 

 tft'initromethylnitraminophenol had formed than is found in the case 

 of tiie other alcohols where it always occurs in small quantities. 



Allyl alcohol, although dried with the greatest care, gave allyl 

 nitrite, but no weighable quantities of ester. Only free phenol was 

 formed. 



Benzyl alcohol, which acted violently, gave products containing 

 benzaldehyde but no benzyl ester of the phenol, only the latter itself. 



Secondary propyl alcohol and sec. butyl alcohol do not yield esters, 

 but the free rrinitromethylnitraminophenol is formed, also the nitrites 

 of those alcohols. 



Tertiary amyl alcohol (amylene hydrate) reacts in an analogous 

 manner. There is formed in addition to some nitrite also amylene. 

 The main product of the reaction consists of phenol. 



In all the above reactions the NOj-group of the nitramine is sub- 

 stituted in the position 3, either by the group OAlk, or by the group OH. 



N^O. n'^^' xN^<^' 



kjlIo v^ila Un, 



NO, / \ NO, NO, / \ NO., NO., / ^ NO., 



\/ NO, "^ '\/ OAlk. ''•■ \/ OH 



NO, NO, NO, 



24^^ 



