The chemistry of cyano-acetylenes. Part VIII. Claisen, amino-Claisen, and thio-Claisen rearrangements in the reactions of cyano-acetylenes with allyl alcohol, prop-2-ynol, allyl amines, and prop-2-enethiol
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 196-200
- https://doi.org/10.1039/j39710000196
Abstract
The Claisen rearrangement was observed in the reaction of (diethylamino) propiolonitrile with allyl alcohol in the presence of boron trifluoride etherate at room temperature. No amino-Claisen rearrangement occurred in the reactions of propiolonitrile, chloropropiolonitrile, or (diethylamino) propiolonitrile with allylamine or diallylamine.The thio-Claisen rearrangement occurred in the reactions of chloropropiolonitrile and (diethylamino)propiolonitrile with prop-2-enethiol at room temperature. Some mechanisms are discussed.Keywords
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