682 
The Philippine Journal of • Science 
1921 
The hexaphenylethane constitution was upheld by Chichi- 
babin . 5 He put forward the instability of trimethylene and its 
homologues as an analogy for the instability of hexaphenylethane. 
Jacobson 6 gave the following constitution to the compound : 
e 
(C 6 H 5 ) 2 = C^Q^C^{C 6 H 5 ) 3 
Flurscheim 7 was in favor of a hexaphenylethane, unstable, 
partly broken down into (CeHsh = C. 
Up to this time one of the chief arguments for an unstable 
hexaphenylethane was the fact that neither the unsymmetrical 
tetraphenylethane nor the pentaphenylethane had been prepared. 
Hence the argument that these compounds were unstable, and 
from analogy hexaphenylethane was also unstable. 
When Gomberg and Cone 8 finally prepared unsymmetrical 
tetraphenylethane and pentaphenylethane and found them to be 
fairly stable, the argument of analogy which had previously in- 
dicated the instability of hexaphenylethane now indicated its 
stability. 
Gomberg 9 then showed that the color formation of the sul- 
phates and chlorides of triphenylcarbinol is intimately connected 
with the change of the benzenoid to the quinoid form. He says : 
Furthermore since the manifestation of color and the salt-like properties 
of these substances are also simultaneous, the conclusion seems warranted 
that both of these phenomena are results of one and the same cause; i.e., 
tautomerization to the quinoid state. Consequently these salts were named 
quinocarbonium salts corresponding to the hypothetical quinocarbonium 
base: 
(C 6 H 5 ) 3 = C-OH 
H 
( — C — 
OH 
For obvious reasons the basicity was now assumed to lie in the quinone 
nucleus in the C * and not in the central carbon atom as had been originally 
supposed. 
' Chichibabin, A. E., Ber. deutsch. chem. Ges. 37 (1904) 4709; Journ. 
f. prak. Chem. 74 (1906) 340. 
“Jacobson, P., Ber. deutsch. chem. Ges. 38 (1905) 196. 
7 Flurscheim, B., Journ. f. prak. Chem. 71 (1905) 505. 
8 Gomberg, M., and Cone, L. H., Ber. deutsch. chem. Ges. 39 (1906) 1461. 
’Gomberg, M., and others, Ber. deutsch. Chem. Ges. 40 (1907) 1847, 
1860; Journ. Am. Chem. Soc. 33 (1911) 540; Ann. d. Chem. 370 (1909) 
190; 376 (1910) 208; Ber. deutsch. chem. Ges. 42 (1909) 406. 
