Conversion of Cycloaliphatic Compounds to Phenols

In this approach a number of monocyclic and bicyclic compounds have served as intermediate and models for the synthesis of phenols and naphthols. Cyclohex-2-enone in tetrahydrofuran containin lithium diethylamide at -78°C has been converted to the 6-phenylselenide by the action of phenylselenyl chloride on the anion.Treatment of the isolated product with 3-chloroperbenzoic acid in tetrahydrofuran (or with 30% hydrogen peroxid in THF) at -15°C for 0.5 hour followed by warming of the reaction mixture to ambient temperature gave phenol in an overall yield of 55% (ref.49). The method was not effective for 

Very different catalytic conditions have been use for the conversion of isophorone in 87% yield to 3,5-xylenol by passage over Cr203-Al203 at 400-600°C (ref.50). 

Thermal treatment of 2-cyclopropylcyclohex-2-enone afforded 2-n-propylphenol (ref.51). 

The enolic trimethylsilyl ether of 1-tetralone with 2,6-lutidine in dichloromethane upon dropwise addition at ambient temperature to a suspension of trityl perchlorate in the same stirred solvent followed by reaction for 1 hour afforded 

The bicyclic cyclohexenone shown, prepared by Diels-Alder addition from 

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