Novel heterocyclic selenazadiphospholaminediselenides, zwitterionic carbamidoyl(phenyl)-phosphinodiselenoic acids and selenoureas derived from cyanamides

Guoxiong Hua, Qingzhi Zhang, Yang Li, Alexandra M. Z. Slawin, J. Derek Woollins

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) reacts with cyanamides (1a-h) in refluxing toluene to afford a series of novel selenazadiphospholaminediselenides (RR'NC=N(PhP(Se)SeP(Se)Ph, R=C6H5(CH2)(1-3), 4-n-C10H21C6H4 and 4-BrC6H4CH2; R'=H, CH3, C2H5 and C(O)OC2H5 2a-g). Post-treatment of the reaction mixture with water led to the formation of carbamidoyl(phenyl)phosphinodiselenoic acids (RR'NC(NH2)P(SeH)(2)Ph, R=C6H5(CH2)(2-3), 4-n-C10H21C6H4 and 4-BrC6H4CH2; R'=H and CH3, 3b, 3c, 3e and 3f) and selenoureas (RR'NC(Se)NH2, R=C6H5(CH)(1-2); R'=CH3 and OC(O)C2H5, 4f and 4h) in moderate to excellent yields. All new compounds are characterised spectroscopically and five X-ray crystal structures are reported. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)6074-6082
Number of pages9
JournalTetrahedron
Volume65
Issue number31
DOIs
Publication statusPublished - 1 Aug 2009

Keywords

  • Woollins' reagent
  • Cyanamides
  • Carbamidoyl(phenyl)phosphinodiselenoic acids
  • Selenazadiphospholaminediselenides
  • Selenoureas
  • PHOSPHORUS-SELENIUM HETEROCYCLES
  • P-SE HETEROCYCLES
  • RAY CRYSTAL-STRUCTURES
  • WOOLLINS REAGENT
  • COMPLEXES
  • REACTIVITY
  • (PHP(SE)(MU-SE))(2)
  • NITRILES

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