ON NON-AROMATIC DIAZONIUM SALTS, 247 
APPENDIX. 
Some Comparative Statistics for British and American Coal Exports for the 
Years 1913 and 1920 respectively. 
In amplification of what has been said in the main Report about the 
threatened loss of our once dominant coal-export trade, the following com- 
parative statistics (recently published in ‘Imperial Commerce and Affairs,’ 
Vol. II., No. 6, pp. 30-31) may be quoted :— 
(1) In the year 1913 the United States exported altogether 20,708,582 tons 
of anthracite and bituminous coals, of which, however, only about 
five million tons went overseas; some 14,482,929 tons of bituminous 
coals went overland into Canada. In the same year Great Britain 
exported to other countries no less than 73,400,118 tons of coal 
(excluding ships’ bunkers). Thus it would appear that in 1913 Great 
Britain sent overseas about fifteen tons of coal to every ton sent 
overseas from the United States. 
(2) In the year 1920 the British coal exports (excluding bunkers) had 
declined to 24,931,853 tons, whilst those of the United States had 
increased to 39,215,030 tons, of which nearly 25 million tons went 
overseas. In other words, whilst our overseas coal trade had shrunk 
to about one-third of its pre-war dimensions, that of the United 
States had increased fivefold. 
(3) The United States has already made great inroads into the European 
coal markets, selling 10,240,422 tons of bituminous coals (besides some 
anthracite) there in 1920. She has also almost captured the Central 
and South American coal markets, where we were once supreme; for 
whilst our coal exports to Central and South America had fallen 
from upwards of 17 million tons in 1913 to rather less than 3.7 million 
tons in 1920, those of the United States had increased something 
like tenfold. 
London, June 30, 1921. Wrtiam A. Bone. 
_Non-aromatic Diazonium Salts.-— Report of Committee (Dr. 
: F. D. Cuarraway, Chairman; Prof. G. T. Moraan, Secretary ; 
Mr. P. G. W. Bayny, and Dr. N. V. Smawicx. Drawn up by 
| Prof. G. T. Moraan and Mr. Henry Burcess). 
Recent investigations have shown that several series of non-aromatic primary amines 
. possess in varying degrees the property of diazotisability. In certain cases the 
existence of a diazo-derivative is inferred from the property of coupling to form 
azo-derivatives or from the fact that the diazo-group can be replaced by other radicals 
such as chlorine, but in other instances diazonium salts have actually been isolated. 
These non-aromatic diazonium salts vary considerably in stability from the excep- 
tionally stable diazonium salts of the pyrazole series 10 the explosive diazo-deriva- 
tives of the thiazole group. Orientation plays an important part in the stability of 
these compounds, as is shown below in the case of the pyrazole and pyridine 
derivatives. 
The requisite properties for diazotisability appear to be the presence of the group 
; H,N—c” and the possession of a certain degree of unsaturation in the cyclic system 
_ in which this carbon atom is included. But it must not be assumed that any base 
_ having the foregoing group and belonging to an unsaturated cyclic system is neces- 
sarily diazotisable. The absence of diazotisability is noteworthy in the thiophen, 
_ furane and pyrrole series in spite of the close relationship between the first of these 
Series and the aromatic compounds. 
} Pyrazole Series. 
In this group the effect of orientation on the stability of the diazonium salts is 
well marked. 4-Amino-3 : 5-dimethylpyrazole when diazotised in the usual manner 
furnishes 3:5-dimethyl pyrazole-4-diazonium chloride stable in hot aqueous solutions 
a 
