✦ LIBER ✦

The reaction of enols with superoxide anion radical [02???]1. Synthesis of 2,3-unsaturated-δ-valerolactones.

✍ Scribed by Aryeh A. Frimer; Pessia Gilinsky-Sharon; Gladis Aljadeff

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 242 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87089-6

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✦ Synopsis

3-and 4-Hydroxycoumarin (& and 2) as well as 2-hydroxy-2,5-cyclohexadien-l-ones a-6 were reacted with K02/18-crown-6 in benzene. Initial deprotonation of the enol hydrogen was followed by nucleophilic attack by 0 sulting anion (for 4 and ,&-q). A convenieng CONDITION* YIELD (2) && KO (5 hr) KOS (16 hr) 89 55 & &% K02 (1.3 hr) 95 &@ &gC KO2 (1 hr) 84 &I& KO (16 hr) KO$ (16 hr) 80 75 z with 0 2 and HO in Benzene REACTION ENOL CONDITIONS* YIELD (z) KO (7 hr) KO$ (16 hr) 78 32 KOH (7 hr) 85 K02 ** K02 (2 hr) 88 KOH (7 hr) 85 K02 ** * Ratio of KX (X=OH or 0 ): 8:2:1 for q and F an % 18-Crown-6: Substrate was 4:2:1 for ga-t, 2:l:l for &, 4:1.5:1 for 116. Reactions were carried out at ambient temperature under ry air. ** The enol cannot be isolated in appreciable yields in this instance because further 1.

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