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Organic Lab Reactions 233

Organic Lab Reactions 233 - 228 THE PREPARATION OF...

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228 THE PREPARATION OF UNSYMMETRICAL BIARYLS dry or moist state, are the reactive intermediates in the diazo reaction and give biaryls when they come in contact with aromatio compounds. On the basis of the analysis of one compound of this 'type, the diazo anhydride structure, RN 2 -~0—N 2 R, was assigned to these compounds. 1 Solutions of the Bodium salts of the diazohydroxides show a similar behavior with aromatic compounds, 4 presumably in virtue of hydrolysis to the diazohydroxides and reaction of the latter with the aromatic compound. R—N=N—ONa + HOH R—N=N—OH + NaOH - R— N=N—OH + R'H -» R—R' + N 2 •+• H 2 O' (R and R' = aryl radicals) The term diazohydroxide will be used to include the so-called diazo anhydrides. When sodium acetate is added to aryldiazonium salts, aryldiazo acetates, R—N=N—OCOCH 3 , are probably formed through rearrange- ment of the aryldiazonium salts initially produced, and they react in the same manner as the aryldiazo hydroxides. The aryldiazo acetates are
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