Diazonium sails

Attention has previously (see Diazonium Sails) been drawn to the fact that unless an excess of hydrochloric (or mineral) acid is used in the diazotisation process, coupling occurs between the diazonium salt and the amine to give diazoamino compounds. Thus phenyldiazonium chloride and aniline yield diazoaminobenzene. This substance may be conveniently prepared by dissolving two equivalents of aniline in three equivalents of hydrochloric acid, and adding one equivalent of sodium nitrite in aqueous solution followed by two equivalents of sodium acetate ... 

Oeaminalion of aromatic amines via diazonium sails, by means of alcohols (Griess), or PO2H3, Sn(OH)2, etc. 

Meerwein arylation. Detailed directions are given for diazolization of p-amino-acelophcnone with 48 % hydrobromic acid and aqueous sodium nitrite in acetone and Meerwein reaction of the diazonium sail in the presence of coppcr(l) bromide (Fisher, reagent grade, washed with acetone until the washings are colorless and dried) with acrylic acid to produce p-acetyl-a-bromohydrocinnamic acid. The yield of white needles, m.p. 159-160°, is, 56-.59 / . 

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