Addition of secondary amines to diacetylenic ketones
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 805-809
- https://doi.org/10.1039/p19720000805
Abstract
Secondary amines add across the free ethynyl group of unsubstituted diacetylenic ketones. Reactions of piperidine with 1-phenylhexa-2,4-diyn-1-one (7), a methyl-substituted derivative, afford 1-phenyl-5-piperidinohex-4-en-2-yn-1-one (17), 3,5-dipiperidinobiphenyl (20), and a diadduct (21); in the presence of water 1-phenyl-3-piperidino-hex-2-ene-1,5-dione (27) is also obtained. Strong solvent-induced shifts, of up to 40 nm, are observed in the u.v. spectra of the adducts. Some unstable alkyl diacetylenic ketones [(4)–(6)] have been obtained.Keywords
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