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Synthesis of Methylene­bicyclo­[3.2.1]­octanol by a Sm(II)-Induced 1,2-Rearrangement Reaction with Ring Expansion of Methylene­bicyclo­[4.2.0]­octanone

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Direct conversion of methylene­bicyclo­[4.2.0]­octanone to methylene­bicyclo­[3.2.1]­octanol by a Sm­(II)-induced 1,2-rearrangement with ring expansion of the methylene­cyclobutane is described. Three conditions were optimized to allow the adaptation of this approach to various substrates. A rearrangement mechanism is proposed involving the generation of a ketyl radical and cyclopentanation by ketyl–olefin cyclization, followed by radical fragmentation and subsequent protonation.

创建时间:
2017-06-29
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