Abstract
Transfer of oxygen atoms from epoxides to triphenylphosphine is efficiently catalyzed by Tp′ReO3 [Tp′ = hydrido-tris -(3,5-dimethylpyrazolyl)borate] in benzene at 75-105 ºC. The reaction tolerates a wide variety of functional groups including ketones (conjugated or non-conjugated to the new double bond), esters, nitriles, ethers, silyl ethers and phthalimides. Relative rates vary with substitution pattern and electronics; in general, monosubstituted and 2,2-disubstituted epoxides react fastest, and cis -2,3-disubstituted systems react faster than trans . Electron-withdrawing substituents promote the reaction.
Key words
epoxide deoxygenation - rhenium catalysis - O-atom transfer
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