Cycloaddition reactions of cumulenes. Part IV. A novel mode of reaction of azomethine oxides with 1,1-dimethylallene; formation of a substituted piperidin-4-one
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 719-721
- https://doi.org/10.1039/p19760000719
Abstract
Reactions of C-aryl-N-alkyl azomethine oxides with 1,1-dimethylallene proceed through an initial 1,3-dipolar cycloaddition, followed by two competing processes: formation of a substituted piperidin-4-one by a further addition reaction of the intermediate with the azomethine oxide and intramolecular rearrangement of the alkylidene-isoxazolidine monoadduct leading to a pyrrolidin-3-one.Keywords
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