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CHEMISTRY: STIEGLITZ AND COLLABORATORS 
valent nitrogen derivatives, the theoretical possibility that another 
path might be taken toward the formation of more stable molecules 
has always been kept in mind. As a consequence, in the investigation 
of every new type of rearrangement, experiments have been included to 
attempt the rearrangement of compounds which could not readily form 
univalent nitrogen derivatives (see an instance above under 3) . From 
this point of view, an attempt was made by the one of us and P. 
N. Leech to rearrange i3-triphenylmethyl-/3-methyl hydroxylamine 
(C6H5)3C.N(CH3)OH by the same methods that had proved successful 
with triphenylmethylhydroxylamine (C6H5)3C.NHOH. Indications of a 
rearrangement and the formation of a methylanihne derivative were 
indeed obtained, but the evidence was quite uncertain, being Kmited 
to a general color reaction for monoalkylanilines and to some melting- 
point determinations of an acetyl derivative of the aniUne. 
We have now succeeded in establishing the fact that jS-triphenyl- 
methyl-/3-methyl hydroxylamine is rearranged in a perfectly normal fash- 
ion by the action of phosphorus pentachloride on the ether solution 
of the hydroxylamine. The compound formed in the reaction was shown 
to be (C6H5)2C(OH)N(CH3) (CeHs) [or its chloride (C6H5)2CC1.N(CH3) 
(CeHs)] by the identification of its products of hydrolysis, methylaniline 
and benzophenone : 
(C6H5)2CCl.N(CH3)(C6H5)+HOH-^(C6H5)2CO-}-C6H5N(CH3)H2Cl. (7) 
The formation of the more important component methylaniline was 
proved (1) by the analysis of its chloroplatinate (found, 31.40% plati- 
num; theory 31.27%); (2) by the comparison of its hydrochloride with 
the hydrochloride of a known preparation of methylaniline (its melting- 
point was 119°-122°, that of the pure hydrochloride the same, and the 
melting-point of a mixture of the two salts the same) ; (3) by the navy 
blue color produced by the action of bleaching powder solution on the 
methylaniline. To these tests may be added the melting-point obser- 
vations made with Leech on the acetyl derivative of the base. The 
benzophenone formed was also isolated and identified by its melting- 
point (47°). 
It was further shown that chlorophenyl-diphenylmethyl-/3-methyl 
hydroxylamine (C1C6H4)(C6H5)2CN(CH3)0H, like the corresponding 
chlorophenyl-diphenylmethylhydroxylamine (ClCeHj (C6H5)2C.NHOH, 
shows a migration of the phenyl group in a fraction of the rearranging 
molecules, a migration of the chlorophenyl radicle in the remainder. 
The molar ratio of methylanihne to chloromethylaniline was 75/25. 
It is, therefore, now for the first time an established fact that sub- 
