Issue 10, 1994

Electrophile-induced cyclisation–fragmentation reactions of oxime O-allyl and O-benzyl ethers

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1994, 1267-1268

Electrophile-induced cyclisation–fragmentation reactions of oxime O-allyl and O-benzyl ethers

R. Grigg, J. Markandu, T. Perrior, Z. Qiong and T. Suzuki, J. Chem. Soc., Chem. Commun., 1994, 1267 DOI: 10.1039/C39940001267

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