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Synlett 1990; 1990(8): 481-483
DOI: 10.1055/s-1990-21135
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A Convenient Approach Towards the Conversion of H-Phosphonate and H-Phosphonothioate Diesters into Phosphoro(di)thioate Derivatives

C. E. Dreef* , C. M. Dreef-Tromp, G. A. van der Marel, J. H. van Boom
  • *Gorlaeus Laboratories, P. O. Box 9502, NL-2300 RA Leiden, The Netherlands
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Publication Date:
08 March 2002 (online)

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S-Benzyl and S-phenyl thiosuccinimides (N-benzylthio-and N-phenylthiosuccinimides) react, in the presence of the base N,N-diisopropylethylamine (DIPEA), with phosphonate and phosphonothioate diesters (HP(O)(OR)2 and HP(S)(OR)2) to give the corresponding S-benzyl(phenyl) phosphorothioates or phosphorodithioates, respectively. Further, S,S-dibenzyl-(diphenyl) phosphorodithioates can be prepared by the reaction of a hydroxylic component with the reactive species generated in situ from ammonium phosphinate, the earlier mentioned individual thiosuccinimides and the activating reagent 2,4,6-triisopropylbenzenesulfonyl chloride.

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