Tools
Tools
Montgomery, Anthony James (1960) A study of reactions of nitrobenzenesulphenyl chlorides. Doctoral thesis, Northern Polytechnic.
The reactions of o-nitrobenzenesulphenyl chloride have been studied. The sulphenyl chloride was added to resorcinol and the resulting dihydroxy-nitrodiphenyl sulphide acetylated, brominated and reduced to the corresponding amino-compound. The diacetoxy-nitrodiphenyl sulphide and the dibromodihydroxy-nitrodiphenyl sulphide were reduced to the corresponding amines and oxidised to the sulphones.
The sulphenyl chloride was added to dimethylaniline and the resulting nitrodiphenyl sulphide brominated and reduced to the corresponding amine. The effect of varying amounts of bromine on this amine (and related compounds) was studied.
The reaction of the sulphenyl chloride with o-chloro- aniline was carried out. The effect of two reducing agents, hydrazine hydrate-palladised charcoal and zinc dust-acetic acid, on the resulting sulphenanilide was studied.
The reaction of the sulphenyl chloride with acetanilide and chloro-substituted acetanilides was studied in an attempt to synthesise diphenyl sulphides.
The addition of some ketones and diketones to the sulphenyl chloride was carried out. The resulting keto and diketo-sulphides were oxidised with hydrogen peroxide to the sulphones or sulphoxides depending on the conditions. All the sulphides, except that obtained by reaction with acetophenone, were split by reduction with stannous chloride and hydrogen chloride in acetic acid. The acetophenone adduct was however reduced under these conditions to the benzothiazine. This was the only successful experiment in preparing a thiazine starting from o-nitro- benzenesulphenyl chloride.
 |
View Item |