Tetrahedron p. 1333 - 1344 (1986)
Update date:2022-08-03
Topics: Acetylenic
Bluthe, Norbert
Gore, Jacques
Malacria, Max
Electrophile initiated acetylenic oxy Cope rearrangement of diversely substituted 5-Hexen-1-yn-3-ols leads to the corresponding αδ-diethylenic aldehydes or ketones in good yields with mainly the E configuration for both double bonds.Silver nitrate and Silver trifluoromethanesulfonate appear to be most suitable electrophiles for this purpose and can be used either stoichiometrically (AgTf) or catalytically (AgNO3).
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