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A New Synthesis of (PhPSe 2 ) 2 (Woollins Reagent) and Its Use in the Synthesis of Novel P–Se Heterocycles
Author(s) -
Gray Ian P.,
Bhattacharyya Pravat,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500291
Subject(s) - reagent , chemistry , yield (engineering) , selenium , ring (chemistry) , ammonia , liquid ammonia , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
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.