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Thermal Rearrangements of<i>N</i>-Aryl-1-alkynesulphenamides into Indoline-2-thiones
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1985
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HeterocyclicTitle SulphenamidesIntermediate ThioketenesOrganic ChemistryThermal RearrangementsStereoselective SynthesisChemistryBromomagnesium BenzenamidesHeterocycle ChemistryPharmacologySynthetic ChemistryEnantioselective Synthesis
Reaction of bromomagnesium benzenamides with 1-alkynyl thiocyanates affords the title sulphenamides. On heating in benzene, these sulphenamides undergo [3.3]-sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding indoline-2-thiones.