Oxidation of Sulfides and Epoxidation of Olefins Caused by the Reaction of Pd-Peroxo or Co-Superoxo Complex with Carboxylic Acid Derivatives

Tadahiko Mashino, Tetsuo Nagano, Masaaki Hirobe

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2 Citations (Scopus)

Abstract

The Pd-peroxo complex (dioxygen)bis(triphenyIphosphine)palladium [Pd(Ph3P)202] caused epoxidation of olefins and oxidations of sulfides and sulfoxides in the presence of carboxylic acid derivatives. The Co-superoxo complex cobalt bis(salicylaldehyde)-3,3/ -diamino-di-n-propylamine [Co(Salpr)02] also oxidized sulfides to sulfoxides during the reaction with carboxylic acid derivatives. These oxidations were dependent upon the presence of a metal-dioxygen complex and an electrophile such as acyl cation. Metal-acylperoxide, generated in situ by the reaction of metal-dioxygen complex with a carboxylic acid derivative, could promote heterolytic cleavage of the 0–0 bond of dioxygen coordinated to metal to form a metal-oxo complex, which seems to be the ultimate species mediating the oxidations.

Original languageEnglish
Pages (from-to)1997-2002
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume36
Issue number6
DOIs
Publication statusPublished - 1988 Jan 1

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Keywords

  • (dioxygen)bis(triphenylphosphine)palladium S-oxidation epoxidation cobalt bis(salicylaldehyde)-3
  • 3'diamino-di-n-propylamine metal-oxo oxene transfer

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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