Journal ArticleDOI
A New Synthesis of (PhPSe2)2 (Woollins Reagent) and Its Use in the Synthesis of Novel P–Se Heterocycles
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TLDR
Four novel phosphorus-selenium heterocycles, including a spirocyclic heterocycle exhibiting a four-membered P2SeC ring, were obtained from the reaction of WR with two reactive substrates (diphenylcyclopropenone and methyl phenylpropiolate).Abstract:
A new and improved method for the preparation of (PhPSe 2 ) 2 (Woollins reagent (WR), 1) is reported. Reaction of dichlorophenylphosphine with Na 2 Se, (prepared from the reaction of elemental selenium and sodium in liquid ammonia) gives WR with excellent purity, high yield and on a larger scale than was previously possible. Four novel phosphorus-selenium heterocycles, including a spirocyclic heterocycle exhibiting a four-membered P 2 SeC ring. were obtained from the reaction of WR with two reactive substrates (diphenylcyclopropenone and methyl phenylpropiolate). Useful selenocarbonyl and thiocarbonyl compounds were obtained from the reaction of both WR and Lawesson's reagent with diphenylcyclopropenone. All new compounds were characterised spectroscopically and three demonstrative X-ray structures are reported.read more
Citations
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Use of Lawesson's reagent in organic syntheses.
Journal ArticleDOI
Recent Advances in Organoselenium Chemistry
TL;DR: In this paper, a microreview highlights new developments of organoselenium chemistry and new selenium compounds as versatile reagents in synthesis, highlighting new developments in organosellium chemistry.
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Formation and Reactivity of Phosphorus–Selenium Rings
Guoxiong Hua,J. Derek Woollins +1 more
TL;DR: Phosphorus-selenium ring chemistry has developed to include the synthesis of some exciting new motifs and provided organic chemists with a new reagent, [PhPSe(2)](2), which has become known as Woollins' reagent.
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Donor–acceptor cyclopropanes with Lawesson's and Woollins' reagents: formation of bisthiophenes and unprecedented cage-like molecules
TL;DR: Furan-derived donor-acceptor-substituted cyclopropanes were reacted with Lawesson's reagent and Woollins' reagent always led to the respective selenium-containing cage-like compounds.
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Dithiophosphonates and related p/s-type ligands of group 11 metals
TL;DR: In this article, a review of the dithiophosphonates and certain related thio species of the group 11 coinage metals, copper, silver and gold, with particular emphasis on structure and coordination modes is presented.
References
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Journal ArticleDOI
Thionation reactions of lawesson's reagents
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Studies on organophosphorus compounds XX. syntheses of thioketones
TL;DR: In this paper, the 13C NMR data of the thiocarbonyls of all thioketones are recorded and a function describing the relation between the chemical shifts of CS and CO is found: δCS1.57 δCO=71.45
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Applications of Lawesson's reagent in organic and organometallic syntheses
TL;DR: The application of Lawesson's reagent [2,4-bis(p-methoxyphenyl)-1, 3-dithiaphosphetane-2, 4-disulfide] in organic and organometallic syntheses is described in this article.
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Selenocarbonyl synthesis using Woollins reagent
TL;DR: In this article, the authors compared secondary and tertiary amides to corresponding selenoamides in 30-70% yields at 130°C in toluene and indolizine-3-aldehydes in 40-59% yield at 25°C.