507236-72-8Relevant academic research and scientific papers
A mild, catalytic, and highly selective method for the oxidation of α,β-enones to 1,4-enediones
Yu, Jin-Quan,Corey
, p. 3232 - 3233 (2003)
A new and simple method is described for the one-step oxidation of α,β-enones to 1,4-enediones in good yields (generally 80-90%) using t-butylhydroperoxide as stoichiometric oxidant and 20% Pd(OH)2 on carbon (5 mol %) as catalyst in CH2Cl2 solution. The same reagents have been used to convert ethylene ketals of α,β-enones to the corresponding monoethylene ketals of 1,4-enediones. Seven representative examples are presented in Table 1. All of the available evidence on these oxidations points to a radical-chain mechanism initiated by the tert-butylperoxy radical (see Scheme 1). γ-tert-Butylperoxy ethers are formed as major products in the oxidation of α,β-enones possessing only a single γ-hydrogen. Copyright
