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Organic Lab Reactions 292

Organic Lab Reactions 292 - CONVERSION TO HYDRAZINE...

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CONVERSION TO HYDRAZINE FOLLOWED BY OXIDATION 287 alkaline formaldehyde method (pp. 283-284), also exists with sodium stannite. It appears, therefore, stannit© should be employed only after failure of the procedures already noted. CONVERSION TO THE HYDRAZINE FOLLOWED BY OXIDATION Reduction of diazonium salts by sodium sulfite or stannous chloride usually produces hydrazines. These compounds may be oxidized to the hydrocarbons, thus providing a deamination sequence. 7 ArNH 2 -* ArN 2 +X- -> ArNHNH 2 -> ArH Although sodium sulfite and stannous chloride are used with about equal frequency in this process, a preference for sodium sulfite is some- times expressed. 110 - m - 112 Stannous chloride occasionally brings about direct replacement of the diazonium group by hydrogen, but this is not a reliable reaction. 118 - 7 - 48 - 114 The hydrazines usually are converted to hydrocarbons by treatment with hot, aqueous cupric sulfate, ferric chloride, or potassium chro- mate.
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