1, 8-Diazabicyclo [5.4. 0] undec-7-ene: a remarkable base in the epoxidation of α,β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH

Yadav, Veejendra K. ; Kapoor, Kamal K. (1995) 1, 8-Diazabicyclo [5.4. 0] undec-7-ene: a remarkable base in the epoxidation of α,β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH Tetrahedron, 51 (31). pp. 8573-8584. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00472-K

Abstract

1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been studied for the epoxidation of electron deficient alkenes with anhydrous t-BuOOH (TBHP) in dichloroethane. Steric demands are higher than that for alkaline H2O2-DBU is recognised as a remarkable base in these oxidations as other bases such as triethyl amine, diisopropylethyl amine, and 1,4-diazabicyclo[2.2.2]octane (DABCO) are absolutely inefficient. DBU is effective in promoting the oxidation of α, β-unsaturated δ-lactones where most of conventional methods either fail or perform poor.

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