Abstract
The reaction between m-chloroperbenzoic acid and phosphabicyclic phosphine oxides (e.g. 8-phenyl-8-oxo-8-phosphabicyclo[3.2.1]oct-6-ene) was investigated and the structure and stereochemistry of the compounds elucidated. It could be shown that compounds possessing the allyl-P(O) R(or Ar) site, in which the double bond is hindered enough to prevent a usual epoxidation, are oxidised by the peracid to the corresponding phosphinate. Furthermore, when the resulting compounds are still strained the phospinates are unstable. The suggested mechanism for the oxidation is a process similar to the Bayer-Villiger oxidation, which is known for ketones.
| Original language | English |
|---|---|
| Pages (from-to) | 45-51 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 31 |
| Issue number | 1 |
| DOIs | |
| State | Published - 1975 |