105752-79-2Relevant academic research and scientific papers
The Chemistry of Acyl- and Sulphonyl-thionitroso Compounds
Meth-Cohn, Otto,Vuuren, Gerda van
, p. 245 - 250 (2007/10/02)
Thiophene S,N-ylides undergo cycloadditions with nucleophilic alkenes to give adducts with concomitant extrusion of acylthionitroso compounds.These new and highly reactive species may be trapped by dienes (to give thiazines by cycloaddition) or by enes (to give acylthiohydroxylamines by ene reaction).With suitable dienes such as isopropene and dimethylbutadiene, the ene reaction competes with the diene addition.In the absence of trap, ethyl thionitrosoformate in aromatic solvents yields bis(ethoxycarbonyl amino) sulphide, while with cyclopentadiene a 2:1 adduct, a rare example of a 1,3,2,4-dithiadiazine, is formed.Thiophene is shown to yield a transient S,N-ylide on treatment with ethoxycarbonylnitrene.
Cycloaddition Reactions of Thiophene S,N-Ylides. A Novel Route to Thionitroso Compounds
Meth-Cohn, Otto,Vuuren, Gerda van
, p. 1144 - 1146 (2007/10/02)
Thiophene S,N-ylides readily react with electron-rich dienophiles yielding adducts formed by the efficient extrusion of acyl- and sulphonyl-thionitroso-compounds, themselves readily trapped by Diels-Alder or ene reactions; similar but slower cycloadditions occur with the analogous S,C-ylides, a potential source of thiocarbonyl derivatives.
