1. Oxidation of a P–C Bond under Mild Conditions.
- Author
-
Ilić, Gordana, Gaguly, Rakesh, Petković, Milena, and Vidović, Dragoslav
- Subjects
- *
BAEYER-Villiger rearrangement , *PYRIDINE , *CARBON-hydrogen bonds , *HYDROGEN peroxide , *PHOSPHINES - Abstract
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. [ABSTRACT FROM AUTHOR]
- Published
- 2015
- Full Text
- View/download PDF