2005
DOI: 10.1002/chin.200543055
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m‐CPBA/KOH: An Efficient Reagent for Nucleophilic Epoxidation of gem‐Deactivated Olefins.

Abstract: Epoxidation O 0218 m-CPBA/KOH: An Efficient Reagent for Nucleophilic Epoxidation of gem-Deactivated Olefins. -MCPBA/KOH as well as MCPBA/K2CO3 are found to be highly efficient and chemoselective combinations for the epoxidation of strongly deactivated olefins bearing two electron-withdrawing groups at the same carbon. They do not affect other double bonds or electrophilic oxidizable centers. -(GARCIA RUANO*, J. L.; FAJARDO, C.; FRAILE, A.; MARTIN*, M. R.; J.

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“…Only the tris(dimethylamino)sulfoxonium was successfully synthesized using this approach. Since m-chloroperoxybenzoate can be used to oxidize electronpoor olefins in CH 2 Cl 2 , 53 we attempted to oxidize the [S(NR 2 ) 3 ][PF 6 ] salts in organic solvents. Though oxidation in pure CH 2 Cl 2 was incomplete, oxidization could be accomplished essentially quantitatively using excess mCPBA/ K 2 CO 3 in a 1:1 mixture of CH 2 Cl 2 :hexanes.…”
Section: ■ Introductionmentioning
confidence: 99%
“…Only the tris(dimethylamino)sulfoxonium was successfully synthesized using this approach. Since m-chloroperoxybenzoate can be used to oxidize electronpoor olefins in CH 2 Cl 2 , 53 we attempted to oxidize the [S(NR 2 ) 3 ][PF 6 ] salts in organic solvents. Though oxidation in pure CH 2 Cl 2 was incomplete, oxidization could be accomplished essentially quantitatively using excess mCPBA/ K 2 CO 3 in a 1:1 mixture of CH 2 Cl 2 :hexanes.…”
Section: ■ Introductionmentioning
confidence: 99%