150 PROCEEDINGS OF THE AMERICAN ACADEMY 



0.2486 gram substance gave 0.4661 gram C0 2 and 0.0861 gram 



H 2 0. 

 0.1855 gram substance gave 0.2865 gram AgCl on ignition with 



CaO. 

 0.2704 gram substance gave 19 c.c. moist nitrogen at 22° and 



750 mm. 



Theory for C 8 H,NC1 2 . Found. 



C 51.06 51.13 



H 3.73 3.84 



N 7.45 7.85 



CI 37.76 38.20 



Isocyan-p-tolylchloride when treated with jo-toluidine is con- 

 verted into _p-tritolylguanidine hydrochloride. In order to obtain 

 the free base, 



.NHC 6 H 4 CH 3 

 CH 3 -C 6 H 4 -N=(r 



X NHC 6 H 4 CH 3 



the solution is made slightly alkaline, and the excess of ^-toluidine 

 driven over with steam. 



The residue was recrystallized from alcohol, and colorless needles 

 obtained, melting at 123°, and identical in every respect with a 

 2)-tritolylguanidiue obtained by Merz and Weith.* 



Cokcluding Remarks. 



A. On Geometrical Isomerism of the Hydroxylamine Derivatives. 



The following new observations have been made in the above 

 experimental portion, which find application in many directions. 



1. That a carbonyl group, ^C-O, can by the addition of water 



attain strong acid properties (p. 123). 2. That a carbonyl group 

 always reacts with phenylhydrazine, forming in the first place an 

 addition product, 



\ / 0H 

 C 



' X NHNHC 6 H 5 



(pp. 121, 131, 148). 3. A spontaneous or easy splitting off of HX, 

 H 2 S, H 2 0, from one and the same carbon atom (p. 137). 4. The 

 conversion of imidechlorides, 



* Zeitschrift fur Cliemie, 1868, p. 610. 



