Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent
Pawel Löwe, Tim Witteler, Fabian Dielmann
Abstract
Phosphorus(v) sulfide and Lawesson's reagent are commonly used thionating reagents which are considered to operate after dissociation into highly reactive dithiophosphorane fragments. We report the synthesis and properties of a monomeric thiophosphonium ion [R2P[double bond, length as m-dash]S]+. The highly electrophilic species reacts with carbonyls in oxo-for-sulfido exchange reactions at room temperature and undergoes phosphorus-chalcogen bond metathesis reactions with phosphine chalcogenides.
Topics & Concepts
ChemistryCationic polymerizationChalcogenElectrophileReagentPhosphineSulfurMetathesisMonomerPolymer chemistryLewis acids and basesIonBase (topology)Organic chemistryInorganic chemistryCatalysisPolymerizationPolymerMathematical analysisMathematicsSynthesis and Reactivity of Sulfur-Containing CompoundsOrganophosphorus compounds synthesisSulfur-Based Synthesis Techniques