105752-74-7Relevant articles and documents
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.