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.
Highlights
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 [R2PQS]+
Phosphorus(V) sulfide (P4S10) and Lawesson’s reagent (I, Scheme 1) are most commonly used in this context.2. Their cyclic structures of alternating sulfur and phosphorus atoms require thermal cleavage into reactive dithiophosphoranes (R-PS2), which can react with carbonyls via four-membered ring intermediates to give the corresponding thiocarbonyls and metathiophosphonates
Summary
Phosphorus(V) sulfide and Lawesson’s reagent are commonly used thionating reagents which are considered to operate after dissociation into highly reactive dithiophosphorane fragments. Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent†
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