Reactions of mono- and bis-N-bromosulfimides with thio-ether crowns, phosphines and selenides

Stephen M. Aucott, Mark R. Bailey, Mark R.J. Elsegood, Liam M. Gilby, Kathryn E. Holmes, Paul F. Kelly, Michael J. Papageorgiou, Sarah Pedrón-Haba

Research output: Contribution to journalArticlepeer-review


The brominated sulfimide Ph2SNBr reacts with diphosphines 1,2-(PPh2)2C2H4 and 1,4-(Ph 2P)2(C6H4) to give the bis-N-phosphoniosulfimidium cations [1,2-(Ph2PNSPh2) 2C2H4]2+ and [1,4-(Ph 2PNSPh2)2(C6H4)] 2+, respectively. Treatment of the bis-sulfimide 1,4-[PhSNH] 2C6H4 with N-bromosuccinimide results in 1,4-[PhSNBr]2C6H4, which in turn reacts with triphenylphosphine to generate [1,4-(PhS{NSPPh3})2C 6H4]Br2. Both Ph2SNBr and 1,4-[PhSNBr]2C6H4 react with the thio-ether crown [9-ane]S3, giving [9[ane]S3NSPh2]Br and [1,4-{[9-ane]S2S(NSPh)2C6H4]Br 2, respectively. The first examples of seleniosulfimidium salts have been isolated from the reactions of Ph2SNBr and 1,4(PhS{NBr}) 2C6H4 with Ph2Se and the structures of the [Ph2SNSePh2]+ and [1,4-(PhSNSePh 2)2C6H4]2+ cations confirmed by X-ray crystallography. Reaction of 1,2-PhS(NH)C6H 4SPh with one equivalent of N-bromosuccinimide followed by addition of Na[BPh4] results in [1,2-(PhS)2(μ-N)C 6H4][BPh4] in which a CCSNS ring is observed; two forms of this material may be isolated upon crystallisation-X-ray crystallography reveals them to differ by the relative orientations of the phenyl rings.

Original languageEnglish (US)
Pages (from-to)959-966
Number of pages8
JournalNew Journal of Chemistry
Issue number8
StatePublished - Aug 2004
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Materials Chemistry


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