Organic Lab Reactions 290

Organic Lab Reactions 290 - USE OF STABILIZED DIAZONIUM...

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USE OF STABILIZED DIAZONIUM. SALTS 285 deaminating agent for unsubstituted amines, their homologs, and ethers, its utility appears to be largely restricted to these substances. USE OF STABILIZED DIAZONIUM SALTS A deamination procedure for which general application is claimed has been described by Hodgson and Ma^sden. 6 An aqueous solution of the diazotized amine is treated with the molar quantity of naphthalene-1,5- disulfonic acid or 2-naphthol-l-sulfonic acid, whereupon the stabilized diazonium compound is precipitated. In most cases the stabilized diazo salts require slight variations in technique for their preparation in optimum yield.* The dry salt is reduced at room temperature in ethanol containing zinc or copper. Overall yields of the order of 90% are reported; however, the purity of the product is not specified. SO 3 H I ArN 2 +X- + | II " 1 -> f I I +H X SO3H ArN 2 + SO 3 - Conversion of stabilized diazo compounds to hydrocarbons does not depend upon the reducing action x)f ethyl alcohol, for the reaction takes
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