Retro-Cope eliminations in the synthesis of 1,2,5-oxadiazinanes from allylamines and nitrones: a method for the amination of unactivated alkenes
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 169-171
- https://doi.org/10.1039/c39930000169
Abstract
Heating an allylamine (e.g.9) and a nitrone (e.g.10) in an inert solvent produces often excellent yields of a 1,2,5-oxadiazinane (e.g.11) by a pathway which features a retro-Cope elimination and a Meisenheimer rearrangement; reduction of the oxadiazinanes leads to vicinal diamines and hence overall amination of the alkene function in the original allylamine.Keywords
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