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

doi:10.1248/cpb.36.1997

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1997-2002
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	36
Issue number	6
DOIs	https://doi.org/10.1248/cpb.36.1997
Publication status	Published - 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

Cite this

Mashino, T., Nagano, T., & Hirobe, M. (1988). Oxidation of Sulfides and Epoxidation of Olefins Caused by the Reaction of Pd-Peroxo or Co-Superoxo Complex with Carboxylic Acid Derivatives. Chemical and Pharmaceutical Bulletin, 36(6), 1997-2002. https://doi.org/10.1248/cpb.36.1997

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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.",

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AU - Hirobe, Masaaki

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N2 - 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.

AB - 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.

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KW - 3'diamino-di-n-propylamine metal-oxo oxene transfer

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Access to Document

10.1248/cpb.36.1997