Publication
Epoxidation of (E,E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with salen-mnIII as the catalyst
| dc.contributor.author | Santos, Clementina M.M. | |
| dc.contributor.author | Silva, Artur | |
| dc.contributor.author | Cavaleiro, José | |
| dc.contributor.author | Lévai, Albert | |
| dc.contributor.author | Patonay, Támas | |
| dc.date.accessioned | 2011-04-04T11:21:31Z | |
| dc.date.available | 2011-04-04T11:21:31Z | |
| dc.date.issued | 2007 | |
| dc.description.abstract | (E,E)-Cinnamylideneacetophenones 3a–j were epoxidized under mild conditions with Jacobsen’s catalyst 4 and hydrogen peroxide or iodosylbenzene as oxidants. γ,δ-Monoepoxides and a diastereomeric mixture of α,β:γ,δ-diepoxides were obtained in each case, and only the α,β-monoepoxide of 4- nitrocinnamylideneacetophenone (3d) was isolated. The presence of a methyl group in the vinylic moiety of substrates 3i,j allowed the formation of two γ,δ-monoepoxide diastereomers. The epoxidation of (E,E)-2 -hydroxycinnamylid- Introduction Salen MnIII complexes are efficient catalysts for the epoxidation of various olefinic compounds.[1–3] Since the pioneering work of Kochi et al.,[4] many contributors have reviewed a wide range of applications of these powerful and selective catalysts.[5–7] Several oxidants have been used as effective oxygen donors in these epoxidations, with iodosylbenzene[ 8–11] and sodium hypochlorite[12–14] being the most frequently reported. Among other common olefin oxidants hydrogen peroxide,[15–17] oxone®,[18] dimethyldioxirane (DMD),[19–23] m-chloroperbenzoic acid (MCPBA),[24] molecular oxygen[25] and more recently also tetrabutylammonium monosulfate[24,26,27] and tetrabutylammonium periodate[ 28] have been used. Alkene epoxidation can also be achieved with simple co-catalysts such as imidazoles, pyridines and tertiary amine N-oxides, which act as axial ligands and, in some cases, as phase-transfer catalysts.[29–31] [a] Department of Agro-Industries, Escola Superior Agrária de Bragança, 5301-855 Bragança, Portugal Fax: +351-273-325405 E-mail: clems@ipb.pt [b] Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal Fax: +351-234-370084 E-mail: arturs@dq.ua.pt [c] Department of Organic Chemistry, University of Debrecen, 4010 Debrecen, Hungary Fax: +36-52-453836 E-mail: alevai@puma.unideb.hu Eur. J. Org. Chem. 2007, 2877–2887 © 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2877 eneacetophenones 3h,j led to the formation of the corresponding γ,δ-monoepoxides as well as (E)-2,3-trans-3-hydroxy- 2-styryl-4-chromanones, which originated from the in situ cyclisation of 2,3-epoxy-1-(2-hydroxyphenyl)-5-phenyl- 4-penten-1-ones. The structures of all new compounds and the stereochemistry of the mono- and diepoxide diastereomers were established by NMR studies. | por |
| dc.identifier.citation | Santos, Clementina; Silva, Artur; Cavaleiro, José; Lévai, Albert; Patonay, Támas (2007). Epoxidation of (E,E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with salen-mnIII as the catalyst. European Journal of Organic Chemistry. ISSN 1434-193X. 17, p. 2877-2887 | por |
| dc.identifier.doi | 10.1002/ejoc.200700123 | |
| dc.identifier.issn | 1434-193X. | |
| dc.identifier.uri | http://hdl.handle.net/10198/3920 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.publisher | Wiley | por |
| dc.subject | Cinnamylideneacetophenones | por |
| dc.subject | Epoxidation | por |
| dc.subject | Jacobsen’s catalyst | por |
| dc.subject | Hydrogen peroxide | por |
| dc.subject | Iodosylbenzene | por |
| dc.title | Epoxidation of (E,E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with salen-mnIII as the catalyst | por |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 2887 | por |
| oaire.citation.startPage | 2877 | por |
| oaire.citation.title | European Journal of Organic Chemistry | por |
| person.familyName | Santos | |
| person.givenName | Clementina M.M. | |
| person.identifier.ciencia-id | 9018-DB9C-C590 | |
| person.identifier.orcid | 0000-0003-4380-7990 | |
| person.identifier.scopus-author-id | 7201458663 | |
| rcaap.rights | openAccess | por |
| rcaap.type | article | por |
| relation.isAuthorOfPublication | 64f662b6-775d-4ea0-bfd7-f527af0ac1a0 | |
| relation.isAuthorOfPublication.latestForDiscovery | 64f662b6-775d-4ea0-bfd7-f527af0ac1a0 |