Publicação
Epoxidation of (E,E)-Cinnamylideneacetophenones Using Salen Mn(III) as Catalyst
| Resumo: | Salen Mn(III) complexes are efficient and practical catalysts for the epoxidation of various α,β-unsaturated carbonyl compounds. Among common oxidants used are iodosylbenzene, sodium hipochlorite, oxone, peracids and dimethyldioxirane [1]. Although the epoxidation of cinnamylideneacetophenones have already been reported in literature (by Julia’s epoxidation using hydrogen peroxide as oxidant [2] and by oxidation with dimethyldioxirane [3]), no studies were performed using these kind of salen Mn(III) complexes as catalysts. On these basis, we developed a study on the epoxidation of cinnamylideneacetophenones 1, catalyzed by commercially available Jacobsen’s catalyst [salen Mn(III)] and using iodosylbenzene and hydrogen peroxide as oxidants. Several experimental conditions have been used and the γ,δ-monoepoxides 2 and, in same cases, the diasteriomeric mixture of α,β:γ,δ-diepoxides 3 have been obtained. In this communication, we report the synthetic details and structural characterisation of the mono 2 and diepoxides 3 obtained. |
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| Autores principais: | Santos, Clementina M.M. |
| Outros Autores: | Silva, Artur; Cavaleiro, José; Patonay, Támas; Lévai, Albert |
| Assunto: | Cinnamylideneacetophenones Salen catalyst Epoxidation Iodosylbenzene Hydrogen peroxide NMR spectroscopy |
| Ano: | 2006 |
| País: | Portugal |
| Tipo de documento: | documento de conferência |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| Resumo: | Salen Mn(III) complexes are efficient and practical catalysts for the epoxidation of various α,β-unsaturated carbonyl compounds. Among common oxidants used are iodosylbenzene, sodium hipochlorite, oxone, peracids and dimethyldioxirane [1]. Although the epoxidation of cinnamylideneacetophenones have already been reported in literature (by Julia’s epoxidation using hydrogen peroxide as oxidant [2] and by oxidation with dimethyldioxirane [3]), no studies were performed using these kind of salen Mn(III) complexes as catalysts. On these basis, we developed a study on the epoxidation of cinnamylideneacetophenones 1, catalyzed by commercially available Jacobsen’s catalyst [salen Mn(III)] and using iodosylbenzene and hydrogen peroxide as oxidants. Several experimental conditions have been used and the γ,δ-monoepoxides 2 and, in same cases, the diasteriomeric mixture of α,β:γ,δ-diepoxides 3 have been obtained. In this communication, we report the synthetic details and structural characterisation of the mono 2 and diepoxides 3 obtained. |
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