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Unusual aromatic hydroxylation in the photooxygenation of 1-isopropylidene-2-indanone and related compounds

✍ Scribed by Harry E. Ensley; P. Balakrishnan; Christopher Hogan

Book ID
104229689
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
214 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

1-Isopropylidene-2-indanone(1) reacts with singlet oxygen in non-nucleophilic solvents to give the epoxyphenol 3. Compound 3 can be deoxygenated by treatment with P(OR),, to afford the regiospecifically hydroxylated phenol 5. The reactivity of a,B-unsaturated carbonyl systems towards singlet oxygen shows a dramatic dependence on the geometry of the enone.' Enones which are constrained to the strans conformation usually fail to react with '0, (,9 > 200) while enones capable of adopting an s-a conformation react readily with '0, (/I = 0.05 to 20).2**3 Footezb has recently reported the reaction of a variety of unsaturated esters with '0, and expressed the reactivity patterns observed in terms of a "gem effect" analogous to the "cis effect" reported earlier by Stephenson.&

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