Aminations of Aromatic Sulfonates with Sodium Amide

Abstract

Amin ations of aromatic su1fonates meno or disulfonate of benzene o-, m-, P-toluene, 4-c, 4rm-, 2-P-xyle, ne., P-ethylbenzene, 1-, 2-, 1, 5-naphth. alenp., , with, sodium amide in liquid ammonia have been studied.
When over two-fold moles of SOdium amide Were used at 80 C er above, the corresponding aromatic primary amines were obtained (Table 2) By gas chropgraphig qpalyses, any iso h amine whides might be fdrmed vria benzyne could not be detected (Table 5). This suggests that the amination is usual aromatie. nucleophilic, subst-itution (SN 2) given in equation (2) The effect of substituents and such reaction conditions as temperature, amounts of sodium amide or liquid ammonia on this reaction were also investigated.