882187-46-4Relevant articles and documents
Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen
Orfanidou, Maria,Petsi, Marina,Zografos, Alexandros L.
supporting information, p. 9172 - 9178 (2021/11/30)
Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.
Monoepoxidation of humulene 2,3-epoxide to humulene 2,3;6,7-diepoxides. Observation of the rotation of the double bond plane by 1H NMR spectral analysis and conformation
Hayano, Kiyoharu,Mochizuki, Katsura
, p. 387 - 393 (2007/10/03)
The reaction of (6E,9E)-humulene 2,3-epoxide (7) with m-CPBA produced two known humulene 2,3;6,7-diepoxides (8 and 9), and careful analysis of the 1H NMR of 7 at various temperatures suggested an equilibrium of four possible conformations, CT,
