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

Research output: Contribution to journal › Article › peer-review

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
Externally published	Yes

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

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.",

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

author = "Tadahiko Mashino and Tetsuo Nagano and Masaaki Hirobe",

year = "1988",

month = jan,

day = "1",

doi = "10.1248/cpb.36.1997",

language = "English",

volume = "36",

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journal = "Chemical and Pharmaceutical Bulletin",

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T1 - Oxidation of Sulfides and Epoxidation of Olefins Caused by the Reaction of Pd-Peroxo or Co-Superoxo Complex with Carboxylic Acid Derivatives

AU - Mashino, Tadahiko

AU - Nagano, Tetsuo

AU - Hirobe, Masaaki

PY - 1988/1/1

Y1 - 1988/1/1

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.

KW - (dioxygen)bis(triphenylphosphine)palladium S-oxidation epoxidation cobalt bis(salicylaldehyde)-3

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

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DO - 10.1248/cpb.36.1997

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EP - 2002

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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