The Organic Chemistry of Nitrogen

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Or the diazo-group may be replaced by iodine, and the product reduced, for example, by distillation over zinc dust. A reaction which is often used for this purpose is Friedlander's. This consists in treating the diazo-salt with an alkaline stannous solution. It has been shown 3 that in this reaction part of the salt is reduced to the hydrazine, which is then oxidized by the rest of the diazo- compound to the hydrocarbon.
4. Halogens. This is effected in various ways : sometimes by heating with
...excess of hydrochloric or hydrobromic acid, or by heating the platinichloride with soda.
The best method is that of Sandmeyer, 4 which consists in heating the chloride or bromide in presence of cuprous chloride or bromide : Ar-N 2 . Br = Ar-Br + N 2 .
1 Remsen, Palmer, Am. Ch. J. 8. 243 (1886) ; Remsen, Dashiell, ib. 15. 105 (1893).
2 Remsen, Palmer, 1. C. ; Cameron, ib. 2O. 229 (1898). 3 Eibner, Bet: 36. 813. 4 Ber. 17. 1633, 2650 (1884).
Reactions of Diazo-compounds 261 The diazo-solution is usually added to the cuprous solution, which has been warmed to a suitable temperature.


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