Abstract
Certain allylic ethers, such as allyl phenyl ether and benzyl phenyl ether undergo allylic carbon-oxygen bond scission with either bis(1,5-cyclopentadiene)nickel(0) or tetrakis(triethylphosphine)nickel(0). Added donors or solvents accelerate these cleavages in the following order: 2,2′-bipyridyl > TMEDA > THF > C 6H 6. Similarly, the aforementioned nickel(0) reagents effect the deoxygenation of epoxides bearing electron-withdrawing substituents and yield the corresponding trans olefins. These observations are interpreted in terms of electron-transfer pathways.
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