522 REPORT—1904. 
between the radicals would now be quite different from those in the normal 
ammonium type. The configuration set forth by the double tetrahedron is the 
labile one, and a tendency therefore exists for it to go over into the stable 
ammonium form (tetrahedron or pyramid), one of the negative radicals being 
replaced by hydrogen or alkyl. 
I think that such pictures are useful in helping us to understand the easy change 
of position of the radicals in quaternary ammonium salts. Further, the complex 
behaviour of pentavalent nitrogen becomes thereby more easily explicable. 
7. On the Products obtained by the Action of Vertiary Bases on some Acid 
Chlorides. By Professor E. WEDEKIND. 
The author has previously shown (‘Annalen,’ 318, 99; 323, 257) that, in spite 
of the violent reaction which occurs between the chlorides of powerful acids and 
strong tertiary bases, no quaternary salt of the type 
/CO.R 
oa \Cl 
is produced, but that the hydrochloride of the tertiary amine, 
H 
Cl 
is obtained in quantitative yield. his fact is in so far of importance in connec- 
tion with the stereochemistry of nitrogen as it indicates the reluctance of the 
trivalent nitrogen atom to take up two acidic or negative groups; the trivalent 
nitrogen atom exhibits a kind of striving to assume the most stable condition, 
that, namely, of which ammonium chloride is the type. 
The question at once arises, in connection with the above reaction, as to what 
becomes of the residue of the acid chloride molecule; the solution of this problem 
presented extraordinary experimental difficulties, but its study has led to the dis- 
covery of several interesting facts, which may here be briefly mentioned. The 
author has already shown that by the action of acetyl chloride on triethylamine, 
pyridine, &c., dehydracetic acid is produced (‘Annalen,’ 323, 247); in this reaction 
four molecules of each component take part, in accordance with the equation 
4CH,.COCI + 4N(C,H,), = 4N(C,H,),1Cl + 0,H,0,(4C,H,0); 
but when the acetic chloride is replaced by propionyl, phenylacetic or hydro- 
cinnamic chloride, products are obtained which have only three times the molecular 
weight of the hypothetical substance which must be supposed to be first formed by 
the splitting off of hydrogen chloride from the one molecule of the acid chloride. 
Thus the condensation product from propionic chloride, CH,.CH,.CO.Cl, has the 
empirical formula C,H,,0, or 3(C,H,O), and that from phenylacetic chloride, 
C,H,.CH,.CO.Cl, corresponds to the formula C,,H,,0, or 3(C,H,0). 
The latter substance proved to be fairly easily obtainable, and the first suppo- 
sition that it might be a phloroglucinol derivative—the symmetrical triphenyl- 
phloroglucinol-—was found untenable, because the material can under no con- 
ditions be reduced to triphenylbenzene, and is relatively very stable even in 
alkaline solutions. The new compound shows simultaneously the behaviour of a 
lactone, a monoketone, and a primary alcohol; thus it gives with soda a monosodio- 
derivative, with hydroxylamine a monoxime, with acetic chloride a monoacetyl 
compound, and with benzoyl chloride a monobenzoyl derivative. On treating it 
with ammonia under pressure it yields a very stable pyridine derivative, and this 
reaction shows it to be a simple homologue of pyronone (the previously known 
rae compounds contain, like dehydracetic acid, a carboxyl group in the side 
chain). 
R,N 
1 On heating with alkalies it yields analogous products of hydrolysis to the 
symmetrical trialkylphloroglucinols. 
