Epoxidation of Electron Deficient Alkenes Using tert-Butyl Hydroperoxide and 1,5,7-Triazabicyclo[4.4.0]dec-5-ene and its Derivatives

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Abstract
The title cyclic guanidine (4a) is an efficient promoter of enone epoxidation by tert-butyl hydroperoxide. Optimisation studies are reported and the procedure applied to cyclic and acyclic ketones, quinones and naphthoquinones. N-Substituted guanidine (4c) proved best for the epoxidation of 2-amidobenzoquinones. Preliminary asymmetric epoxidation studies are also discussed.

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