Tetrahedron Letters p. 1301 - 1304 (1982)
Update date:2022-08-04
Topics:
Frimer, Aryeh A.
Gilinsky-Sharon, Pessia
Aljadeff, Gladis
3- and 4-Hydroxycoumarin (1 and 3) as well as 2-hydroxy-2,5-cyclohexadien-1-ones 5a-f were reacted with KO2/18-crown-6 in benzene.Initial deprotonation of the enol hydrogen was followed by nucleophilic attack by O2<*>> (for 1 and 3) and/or autoxidation of the resulting anion (for 1 and 5a-e).A convenient synthesis of 2,3-unsaturated-δ-valerolactones from the corresponding 2-cyclohexen-1-ones is also described.
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