Use of the salt (C6I5N2Cl)2�SbCl3 in the double-diazonium-salt method

Abstract

1. A double diazonium salt of the composition (C6H6N2Cl)2· has been prepared. 2. When this salt is decomposed with zinc and ethyl acetate, diphenylstibinous chloride is formed in 42–46% yield. 3. When (C6H5N2Cl)2-SbCl3 is decomposed with zinc in acetone, methanol, methyl formate, benzene, chloroform, amyl acetate, or diisopentyl ether, or is decomposed in ethyl acetate with the following metals in powder form; copper, from antimony, aluminum, or magnesium, with the amalgam of aluminum or zinc, or with au alloy of zinc and copper, phenylstibinous dichloride and triphenylstibine dichloride are formed, as well as diphenylated antimony compounds. Triphenylstibine dichloride is the main reaction product in the decomposition of both the salt (C6H5N2Cl)2-SbCl3 and also May's salt with zinc in ethanol. 4. A method has been found for the preparation by the diazo method of triphenylstibine, which is formed in 50% yield by the decomposition with zinc of the reaction mixture containing the double diazonium salt (C6H5N2Cl)2-SbCl3 obtained by diazotizing aniline with sodium nitrate in ethyl acetate in presence of antimony trichloride and hydrochloride acid. 5. When this decomposition reaction is carried out in presence of calcium chloride, triphenylstibine dichloride is obtained in 40% yield.