The reaction of bicyclic phosphine oxides, containing a hindered double bond with m-chloroperbenzoic acid

Y. Kashman, O. Awerbouch

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)45-51
Number of pages7
JournalTetrahedron
Volume31
Issue number1
DOIs
StatePublished - 1975

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