264 THE AROMATIC PRIMARY AMINO GROUP' In addition, a variety of other reducing agents have been employed (see pp. 288-289). USE OF ALCOHOLS In 1864 Griess reported that benzenediazonium salts, upon treatment with boiling ethyl alcohol, yield benzene. 2 C 6 H 6 N 2 +X- + CH 3 CH a OH -» C 6 H 8 + CH 3 CHO + N s + HX The reaction came to be regarded as a general one, in spite of the fact that evidence to the contrary soon began to accumulate. The first irregularity appeared in 1870. It was found that two chlorotoluidines, when diazotized and boiled with ethanol, gave the corre-sponding ethyl ethers; 8 the reaction of a diazonium salt with ethyl alcohol had taken an alternative course. ArN 2 +X- + CH3CH2OH -• ArOCH s CH 3 + N a + HX Later it was found that the decomposition of benzenediazonium salts with ethanol actually yields phenyl ethyl ether contaminated with a little benzene.' This, coupled with the fact that a number of instances of ether formation had been recorded, led to the suggestion that the
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