Oxidation of a P-C Bond under Mild Conditions

Gordana Ilić, Rakesh Gaguly, Milena Petković, Dragoslav Vidović

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7 Citations (Scopus)


The reactivity of phosphenium dication [(Ph3P)2C-P-NiPr2]2+, 12+, towards pyridine N-oxide (O-py) has been investigated. The resulting oxophosphonium dication [(Ph3P)2C(NiPr2)P(O)(O-py)]2+, 22+, was surprisingly stabilized by a less nucleophilic O-py ligand instead of pyridine (py). This compound was then identified as an analogue of the elusive Criegee intermediate as it underwent oxygen insertion into the P-C bond through a mechanism usually observed for Baeyer-Villiger oxidations. This oxygen insertion appears to be the first example of a Baeyer-Villiger oxidation involving O-py.

Original languageEnglish
Pages (from-to)18594-18597
Number of pages4
JournalChemistry - A European Journal
Issue number51
Publication statusPublished - 14 Dec 2015
Externally publishedYes


  • Baeyer-Villiger oxidation
  • Criegee intermediate
  • main-group chemistry
  • P-C bond oxidation
  • phosphenium dication

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