405523-55-9Relevant academic research and scientific papers
Intramolecular epoxidation in unsaturated ketones and oxaziridines
Armstrong,Draffan
, p. 2861 - 2873 (2007/10/03)
The possibility of intramolecular epoxidation in acyclic unsaturated ketones (via dioxiranes) and oxaziridines (via oxaziridinium species) has been investigated. Treatment of several acyclic unsaturated ketones with Oxone led to low levels of regio- and stereocontrol, suggesting that background epoxidation by Oxone dominates. However, treatment of unsaturated oxaziridines with methyl trifluoromethanesulfonate led to intramolecular epoxidation. This process allowed regioselective epoxidation of a non-conjugated diene. It also proceeded with a high degree of stereocontrol consistent with a stereoelectronic preference for aspiro-transition state.
Intramolecular epoxidation of unsaturated oxaziridines
Armstrong, Alan,Draffan, Alistair G.
, p. 646 - 648 (2007/10/03)
Treatment of unsaturated oxaziridines with MeOTf results in intramolecular epoxidation, presumably via oxaziridinium salts. The method has been used to effect regioselective epoxidation of a nonconjugated diene.
