Reaction of p-n-Decyloxybenzenediazonium Fluoborate with Sodium Iodide in Benzene

Abstract

IN an earlier communication¹ it was shown that several diazonium salts belonging to the series, RO.C₆H₄.N₂+}X ⁻, reacted with β-naphthol in benzene containing an equivalent amount of pyridine to form normal azo-compounds. With Grignard reagents, however, p-n-decyloxybenzenediazonium salts gave not only the expected azo compounds but also p-n-decyloxydiphenyl and n-decyloxybenzene which must have been formed from n-decyloxyphenyl radicals produced at an earlier stage. A further instance of the occurrence of radical reactions in the chemistry of diazonium salts has now been found in the reaction of p-n-decyloxybenzenediazonium fluoborate in benzene with sodium iodide dissolved in a small volume of dry acetone. Addition of the sodium iodide solution at the room temperature produced a yellow colour followed by the evolution of nitrogen and formation of p-iode-n-decyloxybenzene and, in addition, free iodine, an equivalent amount of p-n-decyloxydiphenyl, and a trace of diphenyl. The p-n-decyloxydiphenyl must have arisen by production of n-decyloxyphenyl radicals and their subsequent reaction with the medium. The formation of diphenyl requires the intermediate production of phenyl radicals, presumably by reaction of n-decyloxyphenyl radicals with benzene. When the volume of benzene was increased the yield of p-iodo-n-decyloxybenzene was reduced, but both iodine and p-n-decyloxydiphenyl were found in increased, and equivalent, amount.