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- W1980616912 abstract "RuIII(hedta) and RuIII((CH3)2edda)+ (hedta3−=N-hydroxyethylethylenediaminetriacetate; (CH3)2edda2−=N, N− dimethethylethylenediamine-N, N−diacetate) catalyze the epoxidation of cis-stilbene and trans-stilbene using tert- butylhydroperoxide (t-BuOOH) as the oxygen source. Prior spin-trapping studies have documented the existence of LRuIIIO ↔ LRuIVO·− ↔ LRuVO2− character in the species obtained from RuIIIL and to-BuOOH (L=polyam- inopolycarboxylate ligands related to edta4−). The O-atom complex, LRuIIIO, appears responsible for the epoxidation of stilbenes. Yields as high as 63.5% cis-stilbene oxide plus 11.0% trans-stilbene oxide from cis-stilbene and 65.1% cis-stilbene oxide from trans-stilbene (with no trans-stilbene oxide) are formed in the epoxidation reactions. Secondary oxidations of the epoxide products produce between 4 to 8% benzaldehyde depending on conditions. The product distribution using the RuIIIL/t-BuOOH catalyst requires at least three epoxidation pathways: (i) concerted transfer of the oxenoid oxygen to the stilbene nucleophile; this process is favored for cis-stilbene; (ii) an outer-sphere electron transfer from the stilbene to LRuIIIO forming a carbon-centered cation radical adjacent to LRuIIIO·−; this radical pair may couple directly for cis-stilbene or after a rapid isomerization of the trans- stilbene radical; (iii) an acyclic pathway which has both free radical and carbocation resonant character; this allows for isomerism of cis-stilbene to trans-stilbene oxide products. RuIIIO(hedta) is also observed to cleanly oxidize benzaldehyde to benzoic acid, sec-phenetyl alcohol to acetophenone, and benzyl alcohol to benzaldehyde and benzoic acid. Cyclohexene is hydroxylated and further oxidized to 2-cyclohexene-1-one." @default.
- W1980616912 created "2016-06-24" @default.
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- W1980616912 date "1992-03-01" @default.
- W1980616912 modified "2023-10-18" @default.
- W1980616912 title "RuIII(hedta) as an oxygen atom transfer catalyst in the epoxidation of stilbenes" @default.
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- W1980616912 doi "https://doi.org/10.1016/s0020-1693(00)80356-4" @default.
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