Directed Reactions of C-Sulfenyl Halides with 1-Hydroxynaphthalene Derivatives

C-Sulfenyl chlorides react with 1-hydroxynaphthalene derivatives in nitrobenzene with the formation of sulfenylation products sulfenylation. Under the same conditions C-sulfenyl bromides furnish the products of bromination. In the presence of potassium perchlorate the reactions occurs place also in dioxane and acetonitrile with retention of different in reactivity patterns of isostructural chlorides and bromides. In the reaction with 1-hydroxynaphthalene 2-nitro- and 2,4-dinitrobenzenesulfenylbromides both afford the bromination and sulfenylation products in unsimilar ratios