Electrophile-induced cyclisation–fragmentation reactions of oxime O-allyl and O-benzyl ethers
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 10,p. 1267-1268
- https://doi.org/10.1039/c39940001267
Abstract
Phenylselenyl bromide-induced cyclisation of γ- and δ-unsaturated aldoxime and ketoxime O-allyl and O-benzyl ethers is followed by a slow fragmentation furnishing cyclic imines which are readily reduced to pyrrolidines, piperidines or tetrahydroisoquinolines by sodium borohydride; dialkenyl oximes yield quinolizidines by an analogous sequence terminating in a mercury(II)-induced cyclisation.Keywords
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