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Chloromethyl trimethylsilylmethyl sulphide as a parent thiocarbonyl ylide synthon. A simple synthesis of dihydro- and tetrahydro-thiophenes
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1986
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Asymmetric CatalysisCross-coupling ReactionEngineeringAlkene MetathesisChloromethyl Trimethylsilylmethyl SulphideOrganic ChemistryChemistryCaesium FluorideSimple SynthesisParent ThiocarbonylHeterocycle ChemistrySynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringGood Yields
Chloromethyl trimethylsilylmethyl sulphide acts as a parent thiocarbonyl ylide synthon and reacts stereospecifically with activated alkenes and alkynes, catalysed by caesium fluoride, in acetonitrile at room temperature to give tetrahydro- and dihydro-thiophene derivatives in good yields.