20642-83-5Relevant academic research and scientific papers
Copper-catalyzed rearrangement of vinyl oxiranes
Batory, Lindsay A.,McInnis, Christine E.,Njardarson, Jon T.
, p. 16054 - 16055 (2007/10/03)
A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent. Copyright
Isomerization of epoxyalkenes to 2,5-dihydrofurans
-
Example 255, (2008/06/13)
Disclosed are processes for the isomerization of epoxyalkenes to dihydrofurans by contacting an epoxyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst. The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.
Oxymetallation. Part 13. Synthesis of Bicyclic Peroxides via Peroxymercuriation of Cyclic Dienes
Bloodworth, A.J.,Khan, Jamil A.,Loveitt, M.E.
, p. 621 - 632 (2007/10/02)
The bis-mercuriated derivative (12) of 9,10-dioxabicyclodecane has been prepared by peroxymercuriation of cis,cis-octa-1,5-diene, but substantial amounts of bicyclic ethers are also formed in the reaction.The bicyclic peroxides (4) and (5) have been obtained from (12) by reduction and brominolysis respectively. 8,9-Dioxabicyclodecane (6) and the dibromo-derivative (7) have similarly been prepared by peroxymercuriation and demercuriation of cyclo-octa-1,4-diene.It is suggested that the isomeric purity of the peroxides and the concurrent formation of bicyclic ethers both result from equilibrium control of reversible (per)oxymercuriation-de(per)oxymercuriation.A low yield of the -peroxide (8) has been obtained by peroxymercuriation and brominolysis of cyclohexa-1,4-diene, but attempts to prepare -compounds from 5,5-disubstituted cyclopentadienes have been unsuccessful.
