Organophosphorus-Selenium Heteroatom Derivatives from Selenation of Primary/Secondary Amines and Haloalkanes/Dihaloalkanes

Guoxiong Hua, Kasun S. A. Arachchige, Alexandra M. Z. Slawin, J. Derek Woollins*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
1 Downloads (Pure)

Abstract

Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) with four equivalents of primary/secondary amines led to a series of ammonium phenylphosphonamido-diselenoates or phenylphosphonamido-diselenoic diamides 1a-n, the latter further reacted in situ with either two equivalents of haloalkanes or an equimolar amount of dihaloalkane, resulting in formation of the corresponding Se-alkylphenyl-Se-alkylphenyl-phosphonamidodiselenoates 2a-n and alkane bis(N-alkyl-P-phenylphosphonamido-diselenoate) derivatives 3a-n in good to excellent yields. All new compounds have been characterized spectroscopically including multinuclear NMR (H-1, C-13, P-31 and Se-77), IR and mass spectroscopy. Two representative X-ray structures are also described.

Original languageEnglish
Pages (from-to)7402-7410
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2013
Issue number32
Early online date24 Sept 2013
DOIs
Publication statusPublished - Nov 2013

Keywords

  • Woollins' reagent
  • Selenium
  • Phosphorus
  • Amines
  • Haloalkanes
  • Crystal structures

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